色谱手性拆分及其手性识别机理的量子化学研究
|
摘要
本论文应用色谱法和分子模型法相结合研究手性固定相的识别机理,即采用熵焓补偿原理、分子模拟计算和QSERR方法,从分子水平上阐述手性识别的本质,了解手性识别作用在固定相上的部位及其作用力等。
采用气相色谱法在Cyclodex B手性柱上拆分扁桃酸甲酯、α-氯代丙酰替苯胺和α-氯丙酸酯对映异构体,考察了柱温对分离效果影响;通过对映异构体分离过程中的热力学参数的计算,探讨光学异构体分离过程的驱动力和手性识别机理。结果表明所分析的对映异构体在Cyclodex B柱上的分离过程是一个焓驱动过程并存在着焓熵补偿关系。
首次采用运用量子力学PM3方法,成功的模拟研究了天然的β-环糊精和α-氯丙酸乙酯((R/S)-ECPA)主客相互作用,探讨(R/S)-ECPA在β-CD上的手性识别机理。结果表明,(R/S)-ECPA对映体与β-CD形成稳定结合物的结合方式完全不同,(R)-ECPA位于β-CD空腔宽口端,形成缔合物;(S)-ECPA插入β-CD空腔内形成包结物。而且,(S)-ECPA—β-CD的结合稳定能低于(R)-ECPA—β-CD。在(R/S)-ECPA—β-CD结合物中,(R/S)-ECPA中的手性碳接近葡萄糖单元的C(2)和C(3)。则ECPA与β-CD之间的手性识别与葡萄糖单元的C(2)和C(3)所提供的手性环境和ECPA与β-CD结合的紧密程度密切相关。
首次采用运用量子力学PM3方法,模拟研究了运用量子力学PM3方法模拟α-氯丙酸甲酯((R/S)-ECPA)与全甲基-β-环糊(PMBCD)的手性识别过程。结果表明,(R/S)-MCPA对映体与β-CD形成稳定结合物的结合方式完全不同。在(R/S)-MCPA—β-CD结合物中,(R/S)-MCPA中的手性碳接近葡萄糖单元的C(2)和C(3)。则MCPA与PMBCD之间的手性识别与葡萄糖单元的C(2)和C(3)所提供的手性环境和MCPA与PMBCD结合形成的氢键作用模式相关。而且,通过比较作用能之差(ΔE)以预示手性分离色谱流出顺序,其结果与气相色谱实验结果一致。
运用量子化学中的Hartree-Fock程序(6-31G基组)方法计算质子化α-氨基酸溶质的分子结构参数,借助于逐步多元线性回归法建立了α-氨基酸光学异构体在冠醚手性固定相上的色谱保留与其分子结构参数之间的定量结构-对映异构体保留(QSERR)模型。结果表明,α-氨基酸光学异构体的保留因子与溶质的分子结构描述参数之间具有较好的线性相关性。在QSERR模型中,采用的结构参数物理意义明确。所建立的QSERR模型具有较好的稳定性和预测能力。同时,通过QSERR模型探讨了这种冠醚固定相可能的色谱保留和手性识别机理。
In this thesis,the deeper studies of recognition mechanism of chiral stationary phase were carried out by integrating chromatography and molecular modeling method,including the enthalpy-entropy compensation effects of statistic analysis,molecular simulation calculation and QSERRs methods.The nature of chiral recognition was stated from the molecular level in order to understand the positions and the forces of chiral recognition on the stationary phase.
The separation of enantiomers of methyl mandelate,α-chloro-N-phenyl propanamide andα-chloropropionates on the Cyclodex B chiral column containing had been studied by gas chromatography.The effect ofα-chloropropionate structure and column temperature on the separation of enantiomers ofα-chloropropionates had been investigated.On the other hand,the thermodynamic parameters in the process of separation of enantiomers were determined in order to discuss driven power and chiral discrimination mechanism in the process of separation of enantiomers. The experimental results showed that the separation for enantiomers of methyl mandelate,α-chloro-N-phenyl propanamide and α-chloropropionate was enthalpy-driven process and there was enthalpy-entropy compensation.
The host-guest complexation ofβ-cyclodextrin(β-CD) with enantiomers of ethylβ-chloropropionates((R/S)-ECPA) was successfully simulated by Quantum Mechanics PM3 method for the first time.Chiral recognization mechanism of(R/S)-ECPA enantiomers onβ-CD was investigated.The modeling results showed the stabilization complexation structures which formed with(R/S)-ECPA enantiomers andβ-CD were different.(R)-ECPA was located the cavity wide mouth end ofβ-CD to form associated molecule.(S)-ECPA was inserted inβ-CD cavity to form inclusion molecule.The stabilization energy of(S)-ECPA—β-CD complex was less than that of(R)-ECPA—β-CD.And,the chiral carbon in ECPA for(R/S)-ECPA—β-CD complexes was close to C(2) and C(3) in glucose unit.So,the chiral recognization mechanism was closely related to the chiral environment provided to C(2) and C(3) in the glucose unit and hydrogen bond forms of(R/S)-ECPA andβ-CD.
Chiral recognization mechanism of Methylβ-cyclodextrin(PMBCD) with enantiomers of methylα-chloropropionates((R/S)-MCPA was simulated by Quantum Mechanics PM3 method for the first time.The modeling results showed the stabilization complexation structures which formed with(R/S)-MCPA enantiomers and PMBCD were different.The chiral carbon in MCPA for(R/S)-MCPA-β-CD complexes was close to C(2) and C(3) in glucose unit.So,the chiral recognization mechanism was closely related to the chiral environment provided to C(2) and C(3) in the glucose unit and inclusion degree to(R/S)-MCPA andβ-CD.In addition,and the interactive energy diference(ΔE) between two enantiomers was compared to predict the chromatographic elution-order. The results were in accordance with that of GC experiments.
Theα-amino acids soluted-related structure descriptors parameters was computed by Hartree-Fock program(6-31G method) in Quantum chemistry,the QSERR modeling of chromatographic retention of the optical isomers ofα-amino acids on the crown chiral stationary phases and their molecular structure descriptors parameters were set with stepwise multiple linear regression method.The results showed there is better linear relationship between capacity factors of the optical isomers ofα-amino acids and their molecular structure descriptors parameters. The physical meaning of these molecular structure descriptors parameters in the QSERR modeling is definite.The QSERR modeling had better stability and predictability.The chromatographic retention and chiral discrimination mechanism in the separation process of the optical isomers ofα-amino acids on the crown stationary phases were investigated.
采用气相色谱法在Cyclodex B手性柱上拆分扁桃酸甲酯、α-氯代丙酰替苯胺和α-氯丙酸酯对映异构体,考察了柱温对分离效果影响;通过对映异构体分离过程中的热力学参数的计算,探讨光学异构体分离过程的驱动力和手性识别机理。结果表明所分析的对映异构体在Cyclodex B柱上的分离过程是一个焓驱动过程并存在着焓熵补偿关系。
首次采用运用量子力学PM3方法,成功的模拟研究了天然的β-环糊精和α-氯丙酸乙酯((R/S)-ECPA)主客相互作用,探讨(R/S)-ECPA在β-CD上的手性识别机理。结果表明,(R/S)-ECPA对映体与β-CD形成稳定结合物的结合方式完全不同,(R)-ECPA位于β-CD空腔宽口端,形成缔合物;(S)-ECPA插入β-CD空腔内形成包结物。而且,(S)-ECPA—β-CD的结合稳定能低于(R)-ECPA—β-CD。在(R/S)-ECPA—β-CD结合物中,(R/S)-ECPA中的手性碳接近葡萄糖单元的C(2)和C(3)。则ECPA与β-CD之间的手性识别与葡萄糖单元的C(2)和C(3)所提供的手性环境和ECPA与β-CD结合的紧密程度密切相关。
首次采用运用量子力学PM3方法,模拟研究了运用量子力学PM3方法模拟α-氯丙酸甲酯((R/S)-ECPA)与全甲基-β-环糊(PMBCD)的手性识别过程。结果表明,(R/S)-MCPA对映体与β-CD形成稳定结合物的结合方式完全不同。在(R/S)-MCPA—β-CD结合物中,(R/S)-MCPA中的手性碳接近葡萄糖单元的C(2)和C(3)。则MCPA与PMBCD之间的手性识别与葡萄糖单元的C(2)和C(3)所提供的手性环境和MCPA与PMBCD结合形成的氢键作用模式相关。而且,通过比较作用能之差(ΔE)以预示手性分离色谱流出顺序,其结果与气相色谱实验结果一致。
运用量子化学中的Hartree-Fock程序(6-31G基组)方法计算质子化α-氨基酸溶质的分子结构参数,借助于逐步多元线性回归法建立了α-氨基酸光学异构体在冠醚手性固定相上的色谱保留与其分子结构参数之间的定量结构-对映异构体保留(QSERR)模型。结果表明,α-氨基酸光学异构体的保留因子与溶质的分子结构描述参数之间具有较好的线性相关性。在QSERR模型中,采用的结构参数物理意义明确。所建立的QSERR模型具有较好的稳定性和预测能力。同时,通过QSERR模型探讨了这种冠醚固定相可能的色谱保留和手性识别机理。
In this thesis,the deeper studies of recognition mechanism of chiral stationary phase were carried out by integrating chromatography and molecular modeling method,including the enthalpy-entropy compensation effects of statistic analysis,molecular simulation calculation and QSERRs methods.The nature of chiral recognition was stated from the molecular level in order to understand the positions and the forces of chiral recognition on the stationary phase.
The separation of enantiomers of methyl mandelate,α-chloro-N-phenyl propanamide andα-chloropropionates on the Cyclodex B chiral column containing had been studied by gas chromatography.The effect ofα-chloropropionate structure and column temperature on the separation of enantiomers ofα-chloropropionates had been investigated.On the other hand,the thermodynamic parameters in the process of separation of enantiomers were determined in order to discuss driven power and chiral discrimination mechanism in the process of separation of enantiomers. The experimental results showed that the separation for enantiomers of methyl mandelate,α-chloro-N-phenyl propanamide and α-chloropropionate was enthalpy-driven process and there was enthalpy-entropy compensation.
The host-guest complexation ofβ-cyclodextrin(β-CD) with enantiomers of ethylβ-chloropropionates((R/S)-ECPA) was successfully simulated by Quantum Mechanics PM3 method for the first time.Chiral recognization mechanism of(R/S)-ECPA enantiomers onβ-CD was investigated.The modeling results showed the stabilization complexation structures which formed with(R/S)-ECPA enantiomers andβ-CD were different.(R)-ECPA was located the cavity wide mouth end ofβ-CD to form associated molecule.(S)-ECPA was inserted inβ-CD cavity to form inclusion molecule.The stabilization energy of(S)-ECPA—β-CD complex was less than that of(R)-ECPA—β-CD.And,the chiral carbon in ECPA for(R/S)-ECPA—β-CD complexes was close to C(2) and C(3) in glucose unit.So,the chiral recognization mechanism was closely related to the chiral environment provided to C(2) and C(3) in the glucose unit and hydrogen bond forms of(R/S)-ECPA andβ-CD.
Chiral recognization mechanism of Methylβ-cyclodextrin(PMBCD) with enantiomers of methylα-chloropropionates((R/S)-MCPA was simulated by Quantum Mechanics PM3 method for the first time.The modeling results showed the stabilization complexation structures which formed with(R/S)-MCPA enantiomers and PMBCD were different.The chiral carbon in MCPA for(R/S)-MCPA-β-CD complexes was close to C(2) and C(3) in glucose unit.So,the chiral recognization mechanism was closely related to the chiral environment provided to C(2) and C(3) in the glucose unit and inclusion degree to(R/S)-MCPA andβ-CD.In addition,and the interactive energy diference(ΔE) between two enantiomers was compared to predict the chromatographic elution-order. The results were in accordance with that of GC experiments.
Theα-amino acids soluted-related structure descriptors parameters was computed by Hartree-Fock program(6-31G method) in Quantum chemistry,the QSERR modeling of chromatographic retention of the optical isomers ofα-amino acids on the crown chiral stationary phases and their molecular structure descriptors parameters were set with stepwise multiple linear regression method.The results showed there is better linear relationship between capacity factors of the optical isomers ofα-amino acids and their molecular structure descriptors parameters. The physical meaning of these molecular structure descriptors parameters in the QSERR modeling is definite.The QSERR modeling had better stability and predictability.The chromatographic retention and chiral discrimination mechanism in the separation process of the optical isomers ofα-amino acids on the crown stationary phases were investigated.
引文
[1]崔宏杰,吉爱国,李从发.以磺酰化β-环糊精为手性选择剂高效毛细管电泳拆分手性药物中间体[J].中国现代应用药学,2004,21((3)):188
[2]Tucker G.T.,Lennard M.S.Enantiomer specific pharmacokinetics[J].Pharmacol Ther,1990,45(3):309
[3]Adalbert G.R.,Kees G.Current regulatory(draft) guidance on chiral medicinal products:Canada,EEC,Japan,United States[J].Chirality,1994,6(2):72-75
[4]黄量,戴立信,杜灿屏等.药物的化学与生物学[M].北京:化学工业出版社,2002.
[5]陈亿新,刘天穗,刘汝锋等.手性药物技术与展望[J].广州大学学报,2002,1(1):39
[6]李水清,黄延胜.手性化合物对映体拆分方法概述[J].天津化工,2004,18:18-22
[7]惠方民,陈永雷,陈兴国等.糖肽大环抗生素作选择试剂的高效液相色谱和毛细管电泳的手性识别机理[J].分析化学,2004,32(7):964-968
[8]邵保海,徐秀珠,吕建德等.外消旋蔡普生醋类在(S,S)-Whelk-O1与CDMPC 手性柱上的对映体分离及手性识别机理的比较[J].化学学报,2003,61(10):1635-1640
[9]Ma S.,Shen S.,Haddad N.,et al.Chromatographic and spectroscopic studies on the chiral recognition of sulfated β-cyclodextrin as chiral mobile phase additive:Enantiomeric separation of a chiral amine[J].Journal of Chromatography A,2009,1216(8):1232-1240
[10]Shah P.,Hsu T.B.,Rogers L.B.1H and 13C nuclear magnetic resonance studies of enantio-selective hydrogen bonding of fluoroalkyl carbinol by chiral butoxycarbonyl-valine[J].Journal of Chromatography A,1987,396:31-41
[11]张强,刘育.β-环糊精及其衍生物对脂肪族手性对映体及有机染料的分子识别研究[J].高等学校化学学报,2004,25:458-461
[12]Kasat R.B.,Wang N.H.L.,Franses E.I.Experimental probing and modeling of key sorbent-solute interactions of norephedrine enantiomers with polysaccharidebased chiral stationary phases[J].Journal of Chromatography A,2008,1190(1-2):110-119
[13]Bisson W.H.,Abagyan R.,Cavasotto C.N.Molecular basis of agonicity and antagonicity in the androgen receptor studied by molecular dynamics simulations[J].Journal of Molecular Graphics and Modelling,2008,27(4):452-458
[14]Aparoy P.,Leela T.,Reddy R.N.,et al.Computational analysis of R and S isoforms of 12-Lipoxygenases:Homology modeling and docking studies[J].Journal of Molecular Graphics and Modelling,2009,27(6):744-750
[15]Zheng Y.J.Molecular basis for the enantioselective binding of a novel class of cytochrome bcl complex inhibitors[J].Journal of Molecular Graphics and Modelling,2006,25(1):71-76
[16]Zhang Y.,Hidajat K.,Ray A.K.Determination of competitive adsorption isotherm parameters of pindolol enantiomers on a-acid glycoprotein chiral stationary phase[J].Journal of Chromatography A,2006,1131(1-2):176-184
[17]Kenneth W.Busch M.A.B.Chiral Analysis[M].Elsevier Science Ltd 2006.
[18]H(?)berger K.Quantitative structure-(chromatographic) retention relationships[J].Journal of Chromatography A,2007,1158(1-2):273-305
[19]Montanari C.A.,Cass Q.B.,Tiritan M.E.,et al.A QSERR study on enantioselective separation of enantiomeric sulphoxides[J].Analytica Chimica Acta,2000,419(1):93-100
[20]黄可新,马梅玉,尹承烈.L-α-三氟乙酰氧基丙酰氯对外消旋胺及氨基酸的气相色谱拆分[J].有机化学,1995,15:145-149.
[21]Dalgliesh C.E.The synthesis of N-formyl-DL-kynurenine,N-acetyl-DL-kynurenine and related compounds,and observations on the synthesis of kynurenine[J].J.Chem.Soc.,,1952,1:137-141
[22]Pirkle W.H.,Pochapsky T.C.Considerations of chiral recognition relevant to the liquid chromatography separation of enantiomers[J].Chemical Reviews,1989,89(2):347-362
[23]Taylor D.R.,Maher k.Chiral separation by high performance liquid chromatography[J]..J.Chromatogr.Sci.,,1992,30(3):67-71
[24]Aboul E.,Hassan Y.High-performance liquid chromatographic enantioseparation of drugs containing multiple chiral centers on polysaccharide-type chiral stationary phases[J].Journal of Chromatography A,2001,906(1-2):185-193
[25]Okamoto Y.,Yashima E.Polysaccharide Derivatives for Chromatographic Separation of Enantiomers[J].Angewandte Chemie International Edition,1998,37(8):1020-1043
[26]Andersson S.,Allenmark S.,Sanchez D.Chromatographic separation of enantiomers on network-polymeric chiral stationary phases[J].Journal of Chromatography A,1996,741(1):23-31
[27]Hermansson J.Liquid chromatographic resolution of racemic drugs using chiral a-acid glycoprotein column[J].Journal of Chromatography A,1984,298:67-78
[28]Welch C.J.,Szczerba T.,Perrin S.R.Some recent high-performance liquid chromatography separations of the enantiomers of pharmaceuticals and other compounds using the Whelk-O1 chiral stationary phase[J].Journal of Chromatography A,1997,758(1):93-98
[29]Nishi H.Enantioselectivity in chiral capillary electrophoresis with polysaccharides[J].Journal of Chromatography A,1997,792(1-2):327-347
[30]周美杨,凌云,申刚义等.新型噻吩杂环衍生化β-环糊精手性固定相合成及其气相色谱分离性[J].高等学校化学学报,2008,29:493-497
[31]Gottfried Blaschke.Chromatographic Resolution of Racemates.New analytical methods(17)[J].Angewandte Chemie International Edition in English,1980,19(1):13-24
[32]Fanali S.Identification of chiral drug isomers by capillary electrophoresis[J].Journal of Chromatography A,1996,735(1-2):77-121
[33]Wulff G.Molecular Imprinting in Cross-Linked Materials with the Aid of Molecular Templates-A Way towards Artificial Antibodies[J].Angewandte Chemie International Edition in English,1995,34(17):1812-1832
[34]王东新,Malik A.接枝聚硅氧烷环糊精固定相溶胶-凝胶毛细管气相色谱柱分离内酯对映体[J].分析化学,2007,35:360-364
[35]齐素华,艾萍,袁黎明等.β-环糊精衍生物毛细管气相色谱固定相的研究[J].化学研究,2005,16:80-83
[36]Gil-Av E.,Feibush B.,Charles-Sigler R.Separation of enantiomers by gas liquid chromatography with an optically active stationary phase[J].Tetrahedron Letters,1966,7(10):1009-1015
[37]Gil-Av E.,Feibush B.Resolution of enantiomers by gas liquid chromatography with optically active stationary phases.Separation on packed columns[J].Tetrahedron Letters,1967,8(35):3345-3347
[38]Schurig V.,Schmalzing D.,Jung M.,et al.Gas chromatographic enantiomer separation on polysiloxane-anchored permethyl-β-cyclodextrin(Chirasil-Dex)[J].Journal of High Resolution Chromatography,1990,13(10):713-717
[39]Fischer P.,Aichholz R.,B(o|¨)lz U.,et al.Permethyl-β-cyclodextrin,Chemically Bonded to Polysiloxane:a Chiral Stationary Phase with Wider Application Range for Enantiomer Separation by Capillary Gas Chromatography[J].Angewandte Chemie International Edition in English,1990,29(4):427-429
[40]Juvancz Z.,Petersson P.Enantioselective gas chromatography[J].Journal of Microcolumn Separations,1996,8(2):99-114
[41]Koppenhoefer B.,Epperlein U.,Schwierskott M.Enantioseparation of four-membered rings by gas chromatography;an overview[J].Analytical and Bioanalytical Chemistry,1997,359(1):107-114
[42]Juvancz Z.,Alexander G.,J.Szejtli.Permethylated β-cyclodextrin as stationary phase in capillary gas chromatography[J].Journal of High Resolution Chromatography,1987,10(2):105-107
[43]童林荟.环糊精化学[M].北京:科学出版社,2001.
[44]俞惟乐,欧庆瑜.毛细管气相色谱和分离分析新技术[M].北京:科学出版社,1989.
[45]Bicchi C.,D'Amato A.,Rubiolo P.Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oil,aroma and flavour fields[J].Journal of Chromatography A,1999,843(1-2):99-121
[46]Juvancz Z.,Szejtli J.The role of cyclodextrins in chiral selective chromatography[J].TrAC Trends in Analytical Chemistry,2002,21(5):379-388
[47]Crini G.,Lechiri Y.,Janus L.,et al.β-cyclodextrin-copolymers coated on silica beads:Synthesis,characterization and retention behavior in HPLC[J].Chromatographia,1999,50(11):661-669
[48]Bhushan R.,Kumar R.Analytical and preparative enantioseparation of dl-penicillamine and dl-cysteine by high-performance liquid chromatography on α-acid glycoprotein and β-cyclodextrin columns using ninhydrin as a reversible tagging reagent[J].Journal of Chromatography A,2009,1216(15):3413-3417
[49]Wang Y.,Ong T.T.,Li L.S.,et al.Enantioseparation of a novel "click" chemistry derived native β-cyclodextrin chiral stationary phase for high-performance liquid chromatography[J].Journal of Chromatography A,2009,1216(12):2388-2393
[50]阮源萍,张雪曼,陈安齐等.2,6-二-O-戊基-β-环糊精涂渍Symmetry C8柱拆分扁桃酸及其类似物对映体[J].色谱,2004,22(4):420-423
[51]史雪岩,邵青龙,陶丹妮.一种苄基取代的环糊精衍生物的合成及其气相色谱性能研究[J].高等学校化学学报,2001,22(7):1098-1101
[52]Schmidt R.,Wahl H.G.,Dieterich H.J.,et al.Headspace gas chromatographymass spectrometry analysis of isoflurane enantiomers in blood samples after anesthesia with the racemic mixture[J].Chirality,1999,11(3):206-211
[53]Simler D.Chiralse paration of C 8-C12γ-lactoneson ache mically modified cyclodextrin column[J].Analusis,1998,26(1):M27
[54]Juza M.,Braun E.,Schurig V.Preparative enantiomer separation of the inhalation anesthetics enflurane,isoflurane and desflurane by gas chromatography on a derivatized γ-cyclodextrin stationary phase[J].Journal of Chromatography A,1997,769(1):119-127
[55]Schleuder M.,Durrbeck A.,Jira T.The influence of cyclodextrinon the stability of cephalotinand aztreomamin aqueous solution[J].Pharmazie,1998,53(6):381-384
[56]Tak(?)ov(?) E.B.D.,Krup(?)k J.,Ska(?)ni I.,et al.Gas chromatographic separation of PCB atropisomers on cyclodextrin stationary phases[J].Chirality,1998,10(6):540-547
[57]Wiberg K.,Letcher R.,Sandau C.,et al.Enantioselective Gas Chromatography/Mass Spectrometry of Methylsulfonyl PCBs with Application to Arctic Marine Mammals[J].Analytical Chemistry,1998,70(18):3845-3852
[58]Wong C.S.,Garrison A.W.Enantiomer separation of polychlorinated biphenyl atropisomers and polychlorinated biphenyl retention behavior on modified cyclodextrin capillary gas chromatography columns[J].Journal of Chromatography A,2000,866(2):213-220
[59]Quattrini F.,Biressi G.,Juza M.,et al.Enantiomer separation of a-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases[J].Journal of Chromatography A,1999,865(1-2):201-210
[60]于永庆,吴金仙,钱阳俊等.用环糊精毛细管色谱分离卤代芳烃位置异构体[J].化学世界,2000,5:265-267
[61]Terabe S.,Miyashita Y.,Ishihama Y.,et al.Cyclodextrin-modified micellar electrokinetic chromatography:Separation of hydrophobic and enantiomeric compounds [J].Journal of Chromatography A,1993,636(1):47-55
[62]Asztemborska M.,Nowakowski R.,Sybilska D.Separation ability and stoichiometry of cyclodextrin complexes[J].Journal of Chromatography A,2000,902(2):381-387
[63]李良,史雪岩,戴荣继.环糊精类固定相分离二甲萘位置异构体[J].分析化学,2003,31(11):1322 1326
[64]程树华,吴襟,郑国军等.手性气相色谱分离α-醇腈和α-羟基酸对映体[J].分析试验室,2000,19(5):1-4
[65]蒋艳杰,周良模,王清海等.仲醇类对映体衍生物在全甲基-β-环糊精上的拆分研究[J].化学学报,2000,58(2):240-242
[66]陈帆,莫卫民.全丁基2环糊精与硝酸银的混合液作为毛细管气相色谱固定相的研究[J].色谱,2000,18(3):247 250
[67]邓爱华,陈小明,杨拥平.谷氨酸衍生化β-环糊精气相色谱手性固定相的合成及其在毛细管气相色谱中的应用[J].分析化学,2002,30(11):1325-1329
[68]Rongji D.,Ruonong F.,Wei Z.Application of peralkylated β-CDs capillary columns for the GC separation of positional isomers of industrial chemicals[J].Journal of Microcolumn Separations,1995,7(5):455-460
[69]Shitangkoon A.,Vigh G.Systematic modification of the separation selectivity of cyclodextrin-based gas chromatographic stationary phases by varying the size of the 6-O-substituents[J].Journal of Chromatography A,1996,738(1):31-42
[70]Maas B.,Dietrich A.,Mosandl A.Comparison of different 6-tert-butyldimethyl-silylated cyclodextrins as chiral stationary phases in GC[J].Journal of Microcolumn Separations,1996,8(1):47-56
[71]Nie M.Y.,Zhou L.M.,Liu X.L.,et al.Gas chromatographic enantiomer separation on long-chain alkylated β-cyclodextrin chiral stationary phases[J].Analytica Chimica Acta,2000,408(1-2):279-284
[72]Jaus A.,Oehme M.Enantioselective HRGC Separation of Toxaphene Congeners by Ethylated gamma-Cyclodextrins[J].Journal of High Resolution Chromatography,2000,23(4):304-308
[73]Hardt I.,K(o|¨)nig W.A.Diluted versus undiluted cyclodextrin derivates in capillary gas chromatography and the effect of linear carrier gas velocity,Column temperature,and length on enantiomer separation[J].Journal of Microcolumn Separations,1993,5(1):35-40
[74]Dieter S.,Martin J.,Sabine Mo,et al.Extending the scope of enantiomer separations on Chirasil-Dex by GLC:Comparison with permethylated β-cyclodextrin dissolved in OV-1701[J].Journal of High Resolution Chromatography,1992,15(11):723-729
[75]Dietrich A.,Maas B.,Mosandl A.Diluted modified cyclodextrins as chiral capillary gas chromatographic stationary phases:Influence of the polysiloxane solvents on enantioselectivity and column efficiency[J].Journal of Microcolumn Separations,1994,6(1):33-42
[76]Berthod A.,Li W.Y.,Armstrong D.W.Multiple enantioselective retention mechanisms on derivatized cyclodextrin gas chromatographic chiral stationary phases[J].Analytical Chemistry,1992,64(8):873-879
[77]Berg U.,Butkus E.,Frejd T.,et al.Gas Chromatographic Enantioseparation and Thermodynamic Parameters of Bicyclic Diketones.[J].acta.chem,scand,1997,51:1030-1034
[78]Tsutomu Takeichi H.T.,Shigeru Shimura,Yuzi Takayama,Masami Morikawa,.Cyclodextrin carbamates as novel chiral stationary phases for capillary gas chromatography[J].Journal of High Resolution Chromatography,1995,18(3):179-189
[79]Schneider M.,Ballschmiter K.Alkyl nitrates as achiral and chiral solute probes in gas chromatography:Novel properties of a β-cyclodextrin derivative and characterization of its enantioselective forces[J].Journal of Chromatography A,1999,852(2):525-534
[80]Venema A.,Henderiks H.,Geest R.v.The enantioselectivity of modified cyclodextrins:Studies on interaction mechanisms[J].Journal of High Resolution Chromatography,1991,14(10):676-680
[81]Takai K.,Kataoka Y.,Utimoto K.Stereoselective addition of[alpha]-chloro allylic chromium reagents to aldehydes[J].Tetrahedron Letters,1989,30(33):4389-4392
[82]周喜春,吴采樱,陈远萌.冠醚化合物在色谱分析中的应用[J].色谱,1994,12(3):175-179
[83]Ayangar N.R.,A.S.Tambe,Biswas S.S.crowne thers as stationary phasesin gas chromatography,comparison betweend ibenzo-18-crown-6,dibenzo-24-crown-8 and dicyclohexano-24-crown-8 with respect to polarrity、 selectivyand stability[J].J.Chromatogr.,1991,543:179-186
[84]刘玉华,乔冬平,李萌.苯并-15-冠-5 作为气相色谱固定液的研究[J].色谱,1992,10(1):33-35
[85]Cram D.J.,Helgeson R.C.,Sousa L.R.,et al.Chiral recognition in complexation of guests by designed host molecules[J].Pure Appl.Chem.,1975,43(3-4):327-349
[86]Peacock S.S.,Walba D.M.,Gaeta F.C.A.,et al.Host-guest complexation.22.Reciprocal chiral recognition between amino acids and dilocular systems[J].Journal of the American Chemical Society,1980,102(6):2043-2052
[87]Koppenhoefer B.,Nothdurft A.,Pierrot-Sanders J.,et al.CHIRBASE,a graphical molecular database on the separation of enantiomers by liquid-,supercritical fluid-,and gas chromatography[J].Chirality,1993,5(4):213-219
[88]Berthod A.,Chang S.C.,Armstrong D.W.Empirical procedure that uses molecular structure to predict enantioselectivity of chiral stationary phases[J]. Analytical Chemistry,1992,64(4):395-404
[89]Norinder U.,Hermansson J.Chiral separation of N-aminoalkylsuccinimides on an a_1-acid glycoprotein column:A quantitative structure-enantioselectivity relationship study[J].Chirality,1991,3(5):422-426
[90]Kaliszan R.,Noctor T.,Wainer I.Quantitative structure-enationselective retention relationships for the chromatography of 1,4-benzodiazepines on a human serum albumin based HPLC chiral stationary phase:An approach to the computational prediction of retention and enantioselectivity[J].Chromatographia,1992,33(11):546-550
[91]Kaliszan R.,Kaliszan A.,Noctor T.A.G.,et al.Mechanism of retention of benzodiazepines in affinity,reversed-phase and adsorption high-performance liquid chromatography in view of quantitative structure retention relationships[J].Journal of Chromatography A,1992,609(1-2):69-81
[92]Wolf R.M.,Francotte E.,Lohmann D.Quantitative correlation between calculated molecular properties and retention of a series of structurally related racemates on cellulose triacetate[J].J.Chem.Soc.,Perkin Trans.2,1988:893-901
[93]Booth T.D.,Wainer I.W.Investigation of the enantioselective separations of a-alkylarylcarboxylic acids on an amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase using quantitative structure-enantioselective retention relationships Identification of a conformationally driven chiral recognition mechanism[J].Journal of Chromatography A,1996,737(2):157-169
[94]蒋华良,唐斌,陈凯先等.计算机辅助药物分子设计[J].上海:上海科技出版社,1996:
[95]仇缀百,万维,叶德泳等.药物设计学[M].北京:等教育出版社,1999.211-224
[96]Lipkowitz K.B.Theoretical studies of brush-type chiral stationary phases[J].Journal of Chromatography A,1994,666(1-2):493-503
[97]Lipkowitz K.B.Theoretical studies of type Ⅱ-Ⅴ chiral stationary phases[J].Journal of Chromatography A,1995,694(1):15-37
[98]Armstrong D.W.,Ward T.J.,Armstrong R.D.,et al.Separation of Drug Stereoisomers by the Formation of β-Cyclodextrin Inclusion Complexes,Science[J].science,1986,232:1132
[99]Armstrong R.D.,Ward T.J.,Pattabiraman N.,et al.Separation of tamoxifen geometric isomers and metabolites by bonded-phase β-cyclodextrin chromatography [J].Journal of Chromatography:Biomedicai Applications,1987,414:192-196
[100]Armstrong D.W.,Yang X.,Han S.M.,et al.Direct liquid chromatographic separation of racemates with an a-cyclodextrin bonded phase[J].Analytical Chemistry,1987,59(21):2594-2596
[101]Lipkowitz K.B.,Raghothama S.,Yang J.A.Enantioselective binding of tryptophan by a-cyclodextrin[J].Journal of the American Chemical Society,1992,114(5):1554-1562
[102]Kenny B.Lipkowitz C.M.S.Detailed experimental and theoretical analysis of chiral discrimination:Enantioselective binding of R/S methyl mandelate by β-cyclodextrin[J].Chirality,1996,8(4):341-350
[103]Kuroda Y.,Suzuki Y.,He J.,et al.Enantiorecognition of a new chiral selector,-cyclodextrin perphenylcarbamate,as studied by NMR spectroscopy and molecular energy calculation[J].J.Chem.Soc.,Perkin Trans.2,1995:1749-1759
[104]Durham D.G.,Hongxi L.Molecular modelling of the inclusion complexes between β-cyclodextrin and(R)/(S)-methylphenobarbitone and its application to HPLC[J].Chirality,1994,6(4):239-244
[105]David G Durham.Application of force field calculations to the prediction of chirally discriminating chromatographic behaviour for β-CDs[J].Chirality,1996,8(1):58-66
[106]Tesarov(?) E.,Gilar M.,Hobza P.,et al.Correlation between structure of dihydropyridine calcium antagonists and their retention behavior and enantioseparat ion on the β-cyclodextrin stationary phase in HPLC[J].Journal of High Resolution Chromatography,1995,18(9):597-601
[107]Copper C.L.,Davis J.B.,Cole R.O.,et al.Separations of derivatized amino acid enantiomers by cyclodextrin-modified capillary electrophoresis:Mechanistic and molecular modeling studies[J].Electrophoresis,1994,15(1):785-792
[108]K(o|¨)hler J.E.H.,Hohla M.,Richters M.,et al.Cyclodextrin Derivatives as Chiral Selectors investigation of the Interaction with(R,S)-Methyl-2-chloropropionate by Enantioselecfive Gas Chromatography,NMR Spectroscopy,and Molecular Dynamics Simulation[J].Angewandte Chemic International Edition in English,1992,31(3):319-320
[109]K(o|¨)hler J.E.H.,Hohla M.,Richters M.,et al.A Molecular-Dynamics Simulation of the Complex Formation between Methyl(R)/(S)-2-Chloropropionate and Heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin[J].Chemische Berichte,1994,127(1):119-126
[110]Vries N.K.d.,Coussens B.,Meier R.J.,et al.The separation of enantiomers on modified cyclodextrin columns:Measurements and molecular modeling[J].Journal of High Resolution Chromatography,1992,15(8):499-504
[111]Cozzini P.,Domiano P.,Musini P.C.,et al.Molecular modeling as a tool to discriminate between enantiomers resolved by derivatized cyclodextrins in gas chromatography[J].Journal of Inclusion Phenomena and Macrocyclic Chemistry,1996,26(4):295-302
[112]Kobor F.,Angermund K.,Schomburg G.Molecular modelling experiments on chiral recognition in GC with specially derivatized cyclodextrins as selectors[J].Journal of High Resolution Chromatography,1993,16(5):299-311
[113]Beier T.,H(o|¨)ltje H.-D.Modified cyclodextrins as chiral selectors:molecular modelling investigations on the enantioselective binding properties of heptakis(2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl)-β-cyclodextrin[J].Journal of Chromatography B:Biomedical Sciences and Applications,1998,708(1-2):1-20
[114]Lipkowitz K.B.,Pearl G.,Coner B.,et al.Explanation of Where and How Enantioselective Binding Takes Place on Permethylated β-Cyclodextrin,a Chiral Stationary Phase Used in Gas Chromatography[J].Journal of the American ChemicaiSociety,1997,119(3):600-610
[115]Kenny B.Lipkowitz B.C.,Michael A.Peterson,Antonio Morreale,.ENANTIO SELECTIVE BINDING IN GAS CHROMATOGRAPHY:A COMPUTATIONAL STUDY OF CHIRAL SELECTION BYPERMETHYL-β-CYCLODEXTRIN[J].Journal of Physical Organic Chemistry,1997,10(5):311-322
[116]Lipkowitz K.B.,Coner R.,Peterson M.A.Locating Regions of Maximum Chiral Discrimination:A Computational Study of Enantioselection on a Popular Chiral Stationary Phase Used in Chromatography[J].Journal of the American Chemical Society,1997,119(46):11269-11276
[117]Lipkowitz K.B.,Coner R.,Peterson M.A.,et al.The Principle of Maximum Chiral Discrimination:Chiral Recognition in Permethyl-β-cyclodextrin[J].The Journal of Organic Chemistry,1998,63(3):732-745
[118]Reinhardt R.,Richter M.,Mager P.,et al.Investigation of gas chromatographic interaction mechanism on permethylated cyclodextrins by molecular modelling[J]. Chromatographia,1996,43(3):187-194
[119]Black D.R.,Parker C.G.,Zimmerman S.S.,et al.Enantioselective binding of &agr;-pinene and of some cyclohexanetriol derivatives by cyclodextrin hosts:A molecular modeling study[J].Journal of Computational Chemistry,1996,17(8):931-939
[120]Manunza B.,Deiana S.,Pintore M.,et al.A molecular modeling study on the interaction between β-cyclodextrin and synthetic pyretroids[J].Carbohydrate Research,1997,300(1):89-93
[121]Kitae T.,Takashima H.,Kano K.Chiral Recognition of Phenylacetic Acid Derivatives by Aminated Cyclodextrins[J].Journal of Inclusion Phenomena and Macrocyclic Chemistry,1999,33(3):345-359
[122]Alvira E.,Garcfa J.I.,Mayoral J.A.Molecular modelling study for chiral separation of equol enantiomers by β-cyclodextrin[J].Chemical Physics,1999,240(1-2):101-108
[123]Li J.,Carr P.W.Extra-thermodynamic relationships in chromatography enthalpy-entropy compensation in gas chromatography[J].Journal of Chromatography A,1994,670(1-2):105-116
[124]Guillaume Y.C.,Guinchard C.New Statistical Approach to a Gas Chromatography Retention Model: Application to Dichlorophenol Isomers[J].The Journal of Physical Chemistry B,1997,101(41):8390-8394
[125]Stringham R.W.,Blackwell J.A.Factors That Control Successful Entropically Driven Chiral Separations in SFC and HPLC[J].Analytical Chemistry,1997,69(7):1414-1420
[126]王进防,周良模,刘学良等.分子烙印手性固定相分离过程热力学研究[J].高等学校化学学报,2000,6:930-933
[127]Koppenhoefer B.,Bayer E.Chiral recognition in the resolution of enantiomers by GLC[J].Chromatographia,1984,19(1):123-130
[128]周昕.,万宏.,庆瑜欧.2,6-O-二丁基-3-O-三氟乙酰基-γ-环糊精拆分一些氨基酸及分离机理探讨[J].分析化学,1994,22(6):560-564
[129]Aberg G.,MeCullough J.R.,Fang Y.reating urinary incontinence using (s)-deset hyloxybutynin.1997-10-14.
[130]Zhong Q.,Han X.,He L.,et al.Chromatographic evaluation of poly (trans-1,2-cyclohexanediyl-bis-acrylamide) as a chiral stationary phase for HPLC[J].J Chromatogr.A,2005,1066:55
[131]Holder N.L.,Chen T.M.,Matlinger A.C.Applications of ammonium trifluoroacetate as an additive for elution of chiral acids and bases from derivatized polysaccharide stationary phases[J].Chiralty,2005,17:S84
[132]Zhang Y.P.,Lee K.P.,Kim S.-H.Comparative study on the chiral separation of phenyl alcohols by capillary electrophoresis and liquid chromatography[J].Electrophoresis,2004,25:2711
[133]Schurig V.,Negura S.,Mayer S.Enantiomer separation on a Chirasil-Dex-poly-mer -coated stationary phase by conventional and micro-packed high-performance liquid chromatography[J].J Chromatogr.A,1996,755:299
[134]肖美添,黄雅燕,孟春等.扁桃酸甲酯对映体的毛细管电泳手性拆分[J].分析测试学报,2003,5(1):47
[135]黄雅燕,肖美添,石贤爱等.毛细管电泳法测定发酵液中的扁桃酸对映体含量[J].药物分析杂志,2004,24(5):460
[136]申河清,王清海,朱道乾等,七-(2,6-二戊基)-β-环糊精作为毛细管气相色谱固定相分离对映体的研究[J].分析测试学报,1998,17(1):45
[137]聂孟言,周良模,王清海等.扁桃酸及其类似物在全甲基环糊精固定相上的手性拆分[J].分析化学,2000,28(11):1366
[138]Koppenhoefer B.,Koch E.M.,Nicholson G.J.,et al.Chiral recognition of halo carboxylie acid amides studied by gas chromatography on chirasil-val[J].Journal of Chromatography A,1987,406:157-166
[139]Watabe K.Resolution of[alpha]-halogenocarboxylic acid amides on chiral N-lauroyl-[alpha]-(1-naphthyl)ethylamine Effect of the nature of the amide moiety of the solute[J].Journal of Chromatography,1987,399(Part 1):111-119
[140]施介华,徐秀珠,杨根生.反相高效液相色谱法拆分α-氯代丙酰替苯胺光学异构体[J].分析化学,2001,29(4):431-433
[141]McGachy N.T.,Grinberg N.,Variankaval N.Thermodynamic study of N-trifluoroacetyl-O-alkyl nipecotic acid ester enantiomers on diluted permethylated β-cyclodextrin stationary phase[J].Journal of Chromatography A,2005,1064(2):193-204
[142]Reijenga J.C.,Ingelse B.A.,Everaerts F.M.Thermodynamics of chiral selectivity in capillary electrophoresis:separation of ibuprofen enantiomers with b-cyclodextrin[J].J.Chromatogr.A.,,1997,792:371
[143]Maier N.M.,Franco P.,Lindner W.Separation of enantiomers:needs,challenges,perspectives[J].Journal of Chromatog.A,2001,906(1-2):3-33
[144]陈建荣,瞿超进.2-氯丙酸生产技术概况[J].河北工业科技,200219(2):49-51
[145]申桂英.2-氯丙酸[J].精细与专用化学品,2005,13(13):19-20,30
[146]施介华 金迪.,.李祥,周亮.2-氯丙酸及其酯的拆分研究进展[J].浙江工业大学学报,2006,34(5):502-508
[147]Chinchilla R.,Yus M.,Heumann A.Kinetic resolution of racemic carboxylic acids with homochiral alcohols and dicyclohexylcarbodiimide[J].Tetrahedron:Asymmetry,1991,2(2):101-104
[148]Overbeeke P.L.A.,Jongejan J.A.Enantioselectivity of Candida rugosa lipase in the hydrolysis of 2-chloropropionic acid methyl ester[J].Journal of Molecular Catalysis B:Enzymatic,2003,21(1-2):89-91
[149]施介华,金迪一种制备(S)-(-)-2-氯丙酸酯和(R)-(+)-2-氯丙酸的方法.2006.
[150]Watabe K.Resolution of a-halogenocarboxylic acid amides on chiral N-lauroyl-a-(1-naphthyl)ethylamine:Effect of the nature of the amide moiety of the solute[J].Journal of Chromatography A,1987,399:111-119
[151]李俊峰,都婷婷,兰先秋等.柱前衍生化高效液相色谱法准确测定2-氯丙酸的光学纯度[J].分析化学,2007,35(8):1195-1198
[152]Li W.Y.,Jin H.L.,Armstrong D.W.2,6-Di-O-pentyl-3-O-trifluoroacetyl cyclodextrin liquid stationary phases for capillary gas chromatographic separation of enantiomers[J].Journal of Chromatography A,1990,509(2):303-324
[153]Satoshi K.,Tsutomu S.,Yuichi K.,et al.Preparation of optically active compounds by optical resolution via extraction distillation 2005.
[154]Krug R.R.,Hunter W.G.,Grieger R.A.Enthalpy-entropy compensation.1.Some fundamental statistical problems associated with the analysis of van't Hoff and Arrhenius data[J].The Journal of Physical Chemistry,1976,80(21):2335-2341
[155]聂孟言,周良模,王清海等.α-溴丙酸甲酯与β-环糊精衍生物手性识别过程的模拟研究[J].化学学报,2001,59(2):268-273
[156]周英珍,王兴涌,张桂森等.环糊精及其衍生物在手性药物拆分中的应用[J].化学试剂,2006,28(10):590-592,59
[157]施介华,程向炜,周亮等.柱前衍生化法分离3-羟基丁酸乙酯光学异构体[J].分析化学,2007,35(5):714-718
[158]尤长城,赵彦利,刘育.竞争包结法研究β-环糊精及其两种衍生物对一些手性脂肪族客体分子的识别作用[J].高等学校化学学报,2001,22(2):218-222
[159]QI A.d.,LI L.,LIU Y.The Binding Ability and Inclusion Complexation Behavior of Curcumin with Naturalα-,β-,γ-Cyclodextrins and Organoselenium-Brid-ged Bis(β-cyclodextrin) s[J].Journal of Chinese Pharmaceutical Sciences,2003,12(1):15-20
[160]Yah C.,Xiu Z.,Li X.,et al.Molecular modeling study of β-cyclodextrin complexes with(+)-catechin and(-)-epicatechin[J].Journal of Molecular Graphics and Modelling,2007,26(2):420-428
[161]施介华,江峰,王桂林等.酯在聚硅氧烷类固定相上的色谱保留机理研究[J].浙江工业大学学报,2004,32(4):418-422
[162]Lipkowitz K.B.Applications of Computational Chemistry to the Study of Cyclodextrins[J].Chemical Reviews,1998,98(5):1829-1874
[163]Dodziuk H.,Lukin O.,Nowinski K.S.Molecular mechanics calculations of molecular and chiral recognition by cyclodextrins.Is it reliable? The selective complexation of decalins by β-cyclodextrin[J].Journal of Molecular Structure:THEOCHEM,2000,503(3):221-230
[164]Madrid J.M.,Pozuelo J.,Mendicuti F.,et al.Molecular Mechanics Study of the Inclusion Complexes of 2-Methyl Naphthoate with a-and β-Cyclodextrins[J].Journal of Colloid and Interface Science,1997,193(1):112-120
[165]Ding H.,Chao J.,Zhang G.,et al.Preparation and spectral investigation on inclusion complex of[beta]-cyclodextrin with rutin[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2003,59(14):3421-3429
[166]Halgren T.A.MMFF Ⅶ.Characterization of MMFF94,MMFF94s,and other widely available force fields for conformational energies and for intermolecularinteraction energies and geometries[J].Journal of Computational Chemistry,1999,20(7):730-748
[167]Kitagawa M.,Hoshi H.,Sakurai M.,et al.The large dipole moment of cyclomaltohexaose and its role in determining the guest orientation in inclusion complexes[J].Carbohydrate Research,1987,163(1):c1-c3
[168]Huang M.J.,Watts J.D.,Bodor N.Theoretical studies of inclusion complexes of β-cyclodextrin with methylated benzoic acids[J].International Journal of Quantum Chemistry,1997,64(6):711-719
[169]Huang M.-J.,Watts J.D.,Bodor N.Theoretical studies of inclusion complexes of β-cyclodextrin with methylated benzoic acids[J].International Journal of Quantum Chemistry,1997,64(6):711-719
[170]Song K.S.,Hou C.R.,Liu L.,et al.A quantum-chemical study on the molecular recognition of β-cyclodextrin with ground and excited xanthones[J].Journal of Photochemistry and Photobiology A:Chemistry,2001,139(2-3):105-109
[171]Cao Y.,Xiao X.,Ji S.,et al.Study of the inclusion processes of styrene and a-methyl-styrene in β-cyclodextrin[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2004,60(4):815-820
[172]Steiner T.,Koellner G.Crystalline.β-Cyclodextrin Hydrate at Various Humidities:Fast,Continuous,and Reversible Dehydration Studied by X-ray Diffraction[J].Journal of the American Chemical Society,1994,116(12):5122-5128
[173]Frisch M.J.,Trucks G.W.,Schlegel H.B.,et al.Gaussian 03,Gaussian,Inc:Pittsburgh PA,2003.
[174]Liu L.,Li X.S.,Guo Q.X.Orientation conversion in the complexation of a-cyclodextrin with 4-fluorophenol:a PM3 quantum chemical study[J].Journal of Molecular Structure:THEOCHEM,2000,530(1-2):31-37
[175]Saenger W.,Noltemeyer M.,Manor P.C.,et al."Induced-fit"-type complex formation of the model enzyme a-cyclodextrin[J].Bioorganic Chemistry,1976,5(2):187-195
[176]Liu L.,Li X.S.,Song K.S.,et al.PM3 studies on the complexation of a-cyclodextrin with benzaldehyde and acetophenone[J].Journal of Molecular Structure:THEOCHEM,2000,531(1-3):127-134
[177]Alvira E.,Mayoral J.A.,Garcfa J.I.Molecular modelling study of β-cyclodextrin inclusion complexes[J].Chemical Physics Letters,1997,271(1-3):178-184
[178]Kenny B.Lipkowitz B.C.,Michael A.Peterson,Antonio Morreale,.ENANTIO SELECTIVE BINDING IN GAS CHROMATOGRAPHY:A COMPUTATIONAL STUDY OF CHIRAL SELECTION BYPERMETHYL-β-CYCLODEXTRIN[J].Journal of Physical Organic Chemistry,1997,10(5):311-322
[179]缪方明,宿秀梅,徐秀丽.β-环糊精包合物的量子化学计算[J].计算机与应用化学,2002,19(3):315-319
[180]梁文杰.众志成城的氢键 化学中的小矮人[J].CHEMISTRY THE CHINESE CHEM.SOC.,,2004,62(1):
[181]江峰,施介华,严巍等.分子模型及其在手性识别机理研究上的应用[J].分析化学,2004,32(11):1550-1555
[182]高如瑜,王荷芳.QSERRs方法及其在色谱手性识别机理研究中的应用[J].有机化学,1999,19(2):135-140
[183]欧阳亮,何谷,郭丽.一类新型N型钙通道阻滞剂的比较定量构效关系研究[J].化学学报,2006,64:1379-1384
[184]施介华,江峰,严巍等.烃类化合物在不同色谱柱上的定量结构-保留相关性研究[J].分析化学,2005,33(2):181-186
[185]曾小兰,柳红霞,刘红艳.多氯联苯醚的结构参数和热力学性质的密度泛函理论研究[J].化学学报,2007,65:1797
[186]黄君珉,陈慧,高如瑜等.衍生化环糊精键合固定相色谱保留和手性识别机理的研究(Ⅱ)[J].高等学校化学学报,2001,22(11):1838-1842
[187]陈慧,吕宪禹,黄君珉等.衍生化环糊精键合固定相色谱保留和手性识别机理的研究(Ⅰ)[J].高等学校化学学报,2000,21(4):562-565
[188]Suzuki T.,Timofei S.,Iuoras B.E.,et al.Quantitative structure-enantioselective retention relationships for chromatographic separation of arylalkylcarbinols on Pirkle type chiral stationary phases[J].Journal of Chromatography A,2001,922(1-2):13-23
[189]陈娟娟,张大同,沈报春等.D,L-α-氨基酸对映体在冠醚手性柱上的分离[J].分析化学,2006,34(11):1535-1540
[190]Machida Y.,Nishi H.,Nakamura K.,et al.Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether[J].Journal of Chromatography A,1998,805(1-2):85-92
[191]Hyun M.H.,Jin J.S.,Koo H.J.,et al.Liquid chromatographic resolution of racemic amines and amino alcohols on a chiral stationary phase derived from crown ether[J].Journal of Chromatography A,1999,837(1-2):75-82
[192]Hyun M.H.,Han S.C.,Lipshutz B.H.,et al.New chiral crown ether stationary phase for the liquid chromatographic resolution of a-amino acid enantiomers[J].Journal of Chromatography A,2001,910(2):359-365
[193]Sousa L.R.,Sogah G.D.Y.,Hoffman D.H.,et al.Host-guest complexation.12.Total optical resolution of amine and amino ester salts by chromatography[J].Journal of the American Chemical Society,1978,100(14):4569-4576
[194]Matlin S.A.,Tiritan M.E.,Crawford A.J.,et al.HPLC with carbohydrate carbamate chiral phases:Influence of chiral phase structure on enantioselectivity[J].Chirality,1994,6(2):135-140
[195]王鹏.定量构效关系及研究方法[M].哈尔滨工业大学出版社,2004.
[196]Azzaoui K.,Morin-Allory L.Comparison and quantification of chromatographic retention mechanisms on three stationary phases using structure-retention relation ships[J].Chromatographia,1996,42(7):389-395
[2]Tucker G.T.,Lennard M.S.Enantiomer specific pharmacokinetics[J].Pharmacol Ther,1990,45(3):309
[3]Adalbert G.R.,Kees G.Current regulatory(draft) guidance on chiral medicinal products:Canada,EEC,Japan,United States[J].Chirality,1994,6(2):72-75
[4]黄量,戴立信,杜灿屏等.药物的化学与生物学[M].北京:化学工业出版社,2002.
[5]陈亿新,刘天穗,刘汝锋等.手性药物技术与展望[J].广州大学学报,2002,1(1):39
[6]李水清,黄延胜.手性化合物对映体拆分方法概述[J].天津化工,2004,18:18-22
[7]惠方民,陈永雷,陈兴国等.糖肽大环抗生素作选择试剂的高效液相色谱和毛细管电泳的手性识别机理[J].分析化学,2004,32(7):964-968
[8]邵保海,徐秀珠,吕建德等.外消旋蔡普生醋类在(S,S)-Whelk-O1与CDMPC 手性柱上的对映体分离及手性识别机理的比较[J].化学学报,2003,61(10):1635-1640
[9]Ma S.,Shen S.,Haddad N.,et al.Chromatographic and spectroscopic studies on the chiral recognition of sulfated β-cyclodextrin as chiral mobile phase additive:Enantiomeric separation of a chiral amine[J].Journal of Chromatography A,2009,1216(8):1232-1240
[10]Shah P.,Hsu T.B.,Rogers L.B.1H and 13C nuclear magnetic resonance studies of enantio-selective hydrogen bonding of fluoroalkyl carbinol by chiral butoxycarbonyl-valine[J].Journal of Chromatography A,1987,396:31-41
[11]张强,刘育.β-环糊精及其衍生物对脂肪族手性对映体及有机染料的分子识别研究[J].高等学校化学学报,2004,25:458-461
[12]Kasat R.B.,Wang N.H.L.,Franses E.I.Experimental probing and modeling of key sorbent-solute interactions of norephedrine enantiomers with polysaccharidebased chiral stationary phases[J].Journal of Chromatography A,2008,1190(1-2):110-119
[13]Bisson W.H.,Abagyan R.,Cavasotto C.N.Molecular basis of agonicity and antagonicity in the androgen receptor studied by molecular dynamics simulations[J].Journal of Molecular Graphics and Modelling,2008,27(4):452-458
[14]Aparoy P.,Leela T.,Reddy R.N.,et al.Computational analysis of R and S isoforms of 12-Lipoxygenases:Homology modeling and docking studies[J].Journal of Molecular Graphics and Modelling,2009,27(6):744-750
[15]Zheng Y.J.Molecular basis for the enantioselective binding of a novel class of cytochrome bcl complex inhibitors[J].Journal of Molecular Graphics and Modelling,2006,25(1):71-76
[16]Zhang Y.,Hidajat K.,Ray A.K.Determination of competitive adsorption isotherm parameters of pindolol enantiomers on a-acid glycoprotein chiral stationary phase[J].Journal of Chromatography A,2006,1131(1-2):176-184
[17]Kenneth W.Busch M.A.B.Chiral Analysis[M].Elsevier Science Ltd 2006.
[18]H(?)berger K.Quantitative structure-(chromatographic) retention relationships[J].Journal of Chromatography A,2007,1158(1-2):273-305
[19]Montanari C.A.,Cass Q.B.,Tiritan M.E.,et al.A QSERR study on enantioselective separation of enantiomeric sulphoxides[J].Analytica Chimica Acta,2000,419(1):93-100
[20]黄可新,马梅玉,尹承烈.L-α-三氟乙酰氧基丙酰氯对外消旋胺及氨基酸的气相色谱拆分[J].有机化学,1995,15:145-149.
[21]Dalgliesh C.E.The synthesis of N-formyl-DL-kynurenine,N-acetyl-DL-kynurenine and related compounds,and observations on the synthesis of kynurenine[J].J.Chem.Soc.,,1952,1:137-141
[22]Pirkle W.H.,Pochapsky T.C.Considerations of chiral recognition relevant to the liquid chromatography separation of enantiomers[J].Chemical Reviews,1989,89(2):347-362
[23]Taylor D.R.,Maher k.Chiral separation by high performance liquid chromatography[J]..J.Chromatogr.Sci.,,1992,30(3):67-71
[24]Aboul E.,Hassan Y.High-performance liquid chromatographic enantioseparation of drugs containing multiple chiral centers on polysaccharide-type chiral stationary phases[J].Journal of Chromatography A,2001,906(1-2):185-193
[25]Okamoto Y.,Yashima E.Polysaccharide Derivatives for Chromatographic Separation of Enantiomers[J].Angewandte Chemie International Edition,1998,37(8):1020-1043
[26]Andersson S.,Allenmark S.,Sanchez D.Chromatographic separation of enantiomers on network-polymeric chiral stationary phases[J].Journal of Chromatography A,1996,741(1):23-31
[27]Hermansson J.Liquid chromatographic resolution of racemic drugs using chiral a-acid glycoprotein column[J].Journal of Chromatography A,1984,298:67-78
[28]Welch C.J.,Szczerba T.,Perrin S.R.Some recent high-performance liquid chromatography separations of the enantiomers of pharmaceuticals and other compounds using the Whelk-O1 chiral stationary phase[J].Journal of Chromatography A,1997,758(1):93-98
[29]Nishi H.Enantioselectivity in chiral capillary electrophoresis with polysaccharides[J].Journal of Chromatography A,1997,792(1-2):327-347
[30]周美杨,凌云,申刚义等.新型噻吩杂环衍生化β-环糊精手性固定相合成及其气相色谱分离性[J].高等学校化学学报,2008,29:493-497
[31]Gottfried Blaschke.Chromatographic Resolution of Racemates.New analytical methods(17)[J].Angewandte Chemie International Edition in English,1980,19(1):13-24
[32]Fanali S.Identification of chiral drug isomers by capillary electrophoresis[J].Journal of Chromatography A,1996,735(1-2):77-121
[33]Wulff G.Molecular Imprinting in Cross-Linked Materials with the Aid of Molecular Templates-A Way towards Artificial Antibodies[J].Angewandte Chemie International Edition in English,1995,34(17):1812-1832
[34]王东新,Malik A.接枝聚硅氧烷环糊精固定相溶胶-凝胶毛细管气相色谱柱分离内酯对映体[J].分析化学,2007,35:360-364
[35]齐素华,艾萍,袁黎明等.β-环糊精衍生物毛细管气相色谱固定相的研究[J].化学研究,2005,16:80-83
[36]Gil-Av E.,Feibush B.,Charles-Sigler R.Separation of enantiomers by gas liquid chromatography with an optically active stationary phase[J].Tetrahedron Letters,1966,7(10):1009-1015
[37]Gil-Av E.,Feibush B.Resolution of enantiomers by gas liquid chromatography with optically active stationary phases.Separation on packed columns[J].Tetrahedron Letters,1967,8(35):3345-3347
[38]Schurig V.,Schmalzing D.,Jung M.,et al.Gas chromatographic enantiomer separation on polysiloxane-anchored permethyl-β-cyclodextrin(Chirasil-Dex)[J].Journal of High Resolution Chromatography,1990,13(10):713-717
[39]Fischer P.,Aichholz R.,B(o|¨)lz U.,et al.Permethyl-β-cyclodextrin,Chemically Bonded to Polysiloxane:a Chiral Stationary Phase with Wider Application Range for Enantiomer Separation by Capillary Gas Chromatography[J].Angewandte Chemie International Edition in English,1990,29(4):427-429
[40]Juvancz Z.,Petersson P.Enantioselective gas chromatography[J].Journal of Microcolumn Separations,1996,8(2):99-114
[41]Koppenhoefer B.,Epperlein U.,Schwierskott M.Enantioseparation of four-membered rings by gas chromatography;an overview[J].Analytical and Bioanalytical Chemistry,1997,359(1):107-114
[42]Juvancz Z.,Alexander G.,J.Szejtli.Permethylated β-cyclodextrin as stationary phase in capillary gas chromatography[J].Journal of High Resolution Chromatography,1987,10(2):105-107
[43]童林荟.环糊精化学[M].北京:科学出版社,2001.
[44]俞惟乐,欧庆瑜.毛细管气相色谱和分离分析新技术[M].北京:科学出版社,1989.
[45]Bicchi C.,D'Amato A.,Rubiolo P.Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oil,aroma and flavour fields[J].Journal of Chromatography A,1999,843(1-2):99-121
[46]Juvancz Z.,Szejtli J.The role of cyclodextrins in chiral selective chromatography[J].TrAC Trends in Analytical Chemistry,2002,21(5):379-388
[47]Crini G.,Lechiri Y.,Janus L.,et al.β-cyclodextrin-copolymers coated on silica beads:Synthesis,characterization and retention behavior in HPLC[J].Chromatographia,1999,50(11):661-669
[48]Bhushan R.,Kumar R.Analytical and preparative enantioseparation of dl-penicillamine and dl-cysteine by high-performance liquid chromatography on α-acid glycoprotein and β-cyclodextrin columns using ninhydrin as a reversible tagging reagent[J].Journal of Chromatography A,2009,1216(15):3413-3417
[49]Wang Y.,Ong T.T.,Li L.S.,et al.Enantioseparation of a novel "click" chemistry derived native β-cyclodextrin chiral stationary phase for high-performance liquid chromatography[J].Journal of Chromatography A,2009,1216(12):2388-2393
[50]阮源萍,张雪曼,陈安齐等.2,6-二-O-戊基-β-环糊精涂渍Symmetry C8柱拆分扁桃酸及其类似物对映体[J].色谱,2004,22(4):420-423
[51]史雪岩,邵青龙,陶丹妮.一种苄基取代的环糊精衍生物的合成及其气相色谱性能研究[J].高等学校化学学报,2001,22(7):1098-1101
[52]Schmidt R.,Wahl H.G.,Dieterich H.J.,et al.Headspace gas chromatographymass spectrometry analysis of isoflurane enantiomers in blood samples after anesthesia with the racemic mixture[J].Chirality,1999,11(3):206-211
[53]Simler D.Chiralse paration of C 8-C12γ-lactoneson ache mically modified cyclodextrin column[J].Analusis,1998,26(1):M27
[54]Juza M.,Braun E.,Schurig V.Preparative enantiomer separation of the inhalation anesthetics enflurane,isoflurane and desflurane by gas chromatography on a derivatized γ-cyclodextrin stationary phase[J].Journal of Chromatography A,1997,769(1):119-127
[55]Schleuder M.,Durrbeck A.,Jira T.The influence of cyclodextrinon the stability of cephalotinand aztreomamin aqueous solution[J].Pharmazie,1998,53(6):381-384
[56]Tak(?)ov(?) E.B.D.,Krup(?)k J.,Ska(?)ni I.,et al.Gas chromatographic separation of PCB atropisomers on cyclodextrin stationary phases[J].Chirality,1998,10(6):540-547
[57]Wiberg K.,Letcher R.,Sandau C.,et al.Enantioselective Gas Chromatography/Mass Spectrometry of Methylsulfonyl PCBs with Application to Arctic Marine Mammals[J].Analytical Chemistry,1998,70(18):3845-3852
[58]Wong C.S.,Garrison A.W.Enantiomer separation of polychlorinated biphenyl atropisomers and polychlorinated biphenyl retention behavior on modified cyclodextrin capillary gas chromatography columns[J].Journal of Chromatography A,2000,866(2):213-220
[59]Quattrini F.,Biressi G.,Juza M.,et al.Enantiomer separation of a-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases[J].Journal of Chromatography A,1999,865(1-2):201-210
[60]于永庆,吴金仙,钱阳俊等.用环糊精毛细管色谱分离卤代芳烃位置异构体[J].化学世界,2000,5:265-267
[61]Terabe S.,Miyashita Y.,Ishihama Y.,et al.Cyclodextrin-modified micellar electrokinetic chromatography:Separation of hydrophobic and enantiomeric compounds [J].Journal of Chromatography A,1993,636(1):47-55
[62]Asztemborska M.,Nowakowski R.,Sybilska D.Separation ability and stoichiometry of cyclodextrin complexes[J].Journal of Chromatography A,2000,902(2):381-387
[63]李良,史雪岩,戴荣继.环糊精类固定相分离二甲萘位置异构体[J].分析化学,2003,31(11):1322 1326
[64]程树华,吴襟,郑国军等.手性气相色谱分离α-醇腈和α-羟基酸对映体[J].分析试验室,2000,19(5):1-4
[65]蒋艳杰,周良模,王清海等.仲醇类对映体衍生物在全甲基-β-环糊精上的拆分研究[J].化学学报,2000,58(2):240-242
[66]陈帆,莫卫民.全丁基2环糊精与硝酸银的混合液作为毛细管气相色谱固定相的研究[J].色谱,2000,18(3):247 250
[67]邓爱华,陈小明,杨拥平.谷氨酸衍生化β-环糊精气相色谱手性固定相的合成及其在毛细管气相色谱中的应用[J].分析化学,2002,30(11):1325-1329
[68]Rongji D.,Ruonong F.,Wei Z.Application of peralkylated β-CDs capillary columns for the GC separation of positional isomers of industrial chemicals[J].Journal of Microcolumn Separations,1995,7(5):455-460
[69]Shitangkoon A.,Vigh G.Systematic modification of the separation selectivity of cyclodextrin-based gas chromatographic stationary phases by varying the size of the 6-O-substituents[J].Journal of Chromatography A,1996,738(1):31-42
[70]Maas B.,Dietrich A.,Mosandl A.Comparison of different 6-tert-butyldimethyl-silylated cyclodextrins as chiral stationary phases in GC[J].Journal of Microcolumn Separations,1996,8(1):47-56
[71]Nie M.Y.,Zhou L.M.,Liu X.L.,et al.Gas chromatographic enantiomer separation on long-chain alkylated β-cyclodextrin chiral stationary phases[J].Analytica Chimica Acta,2000,408(1-2):279-284
[72]Jaus A.,Oehme M.Enantioselective HRGC Separation of Toxaphene Congeners by Ethylated gamma-Cyclodextrins[J].Journal of High Resolution Chromatography,2000,23(4):304-308
[73]Hardt I.,K(o|¨)nig W.A.Diluted versus undiluted cyclodextrin derivates in capillary gas chromatography and the effect of linear carrier gas velocity,Column temperature,and length on enantiomer separation[J].Journal of Microcolumn Separations,1993,5(1):35-40
[74]Dieter S.,Martin J.,Sabine Mo,et al.Extending the scope of enantiomer separations on Chirasil-Dex by GLC:Comparison with permethylated β-cyclodextrin dissolved in OV-1701[J].Journal of High Resolution Chromatography,1992,15(11):723-729
[75]Dietrich A.,Maas B.,Mosandl A.Diluted modified cyclodextrins as chiral capillary gas chromatographic stationary phases:Influence of the polysiloxane solvents on enantioselectivity and column efficiency[J].Journal of Microcolumn Separations,1994,6(1):33-42
[76]Berthod A.,Li W.Y.,Armstrong D.W.Multiple enantioselective retention mechanisms on derivatized cyclodextrin gas chromatographic chiral stationary phases[J].Analytical Chemistry,1992,64(8):873-879
[77]Berg U.,Butkus E.,Frejd T.,et al.Gas Chromatographic Enantioseparation and Thermodynamic Parameters of Bicyclic Diketones.[J].acta.chem,scand,1997,51:1030-1034
[78]Tsutomu Takeichi H.T.,Shigeru Shimura,Yuzi Takayama,Masami Morikawa,.Cyclodextrin carbamates as novel chiral stationary phases for capillary gas chromatography[J].Journal of High Resolution Chromatography,1995,18(3):179-189
[79]Schneider M.,Ballschmiter K.Alkyl nitrates as achiral and chiral solute probes in gas chromatography:Novel properties of a β-cyclodextrin derivative and characterization of its enantioselective forces[J].Journal of Chromatography A,1999,852(2):525-534
[80]Venema A.,Henderiks H.,Geest R.v.The enantioselectivity of modified cyclodextrins:Studies on interaction mechanisms[J].Journal of High Resolution Chromatography,1991,14(10):676-680
[81]Takai K.,Kataoka Y.,Utimoto K.Stereoselective addition of[alpha]-chloro allylic chromium reagents to aldehydes[J].Tetrahedron Letters,1989,30(33):4389-4392
[82]周喜春,吴采樱,陈远萌.冠醚化合物在色谱分析中的应用[J].色谱,1994,12(3):175-179
[83]Ayangar N.R.,A.S.Tambe,Biswas S.S.crowne thers as stationary phasesin gas chromatography,comparison betweend ibenzo-18-crown-6,dibenzo-24-crown-8 and dicyclohexano-24-crown-8 with respect to polarrity、 selectivyand stability[J].J.Chromatogr.,1991,543:179-186
[84]刘玉华,乔冬平,李萌.苯并-15-冠-5 作为气相色谱固定液的研究[J].色谱,1992,10(1):33-35
[85]Cram D.J.,Helgeson R.C.,Sousa L.R.,et al.Chiral recognition in complexation of guests by designed host molecules[J].Pure Appl.Chem.,1975,43(3-4):327-349
[86]Peacock S.S.,Walba D.M.,Gaeta F.C.A.,et al.Host-guest complexation.22.Reciprocal chiral recognition between amino acids and dilocular systems[J].Journal of the American Chemical Society,1980,102(6):2043-2052
[87]Koppenhoefer B.,Nothdurft A.,Pierrot-Sanders J.,et al.CHIRBASE,a graphical molecular database on the separation of enantiomers by liquid-,supercritical fluid-,and gas chromatography[J].Chirality,1993,5(4):213-219
[88]Berthod A.,Chang S.C.,Armstrong D.W.Empirical procedure that uses molecular structure to predict enantioselectivity of chiral stationary phases[J]. Analytical Chemistry,1992,64(4):395-404
[89]Norinder U.,Hermansson J.Chiral separation of N-aminoalkylsuccinimides on an a_1-acid glycoprotein column:A quantitative structure-enantioselectivity relationship study[J].Chirality,1991,3(5):422-426
[90]Kaliszan R.,Noctor T.,Wainer I.Quantitative structure-enationselective retention relationships for the chromatography of 1,4-benzodiazepines on a human serum albumin based HPLC chiral stationary phase:An approach to the computational prediction of retention and enantioselectivity[J].Chromatographia,1992,33(11):546-550
[91]Kaliszan R.,Kaliszan A.,Noctor T.A.G.,et al.Mechanism of retention of benzodiazepines in affinity,reversed-phase and adsorption high-performance liquid chromatography in view of quantitative structure retention relationships[J].Journal of Chromatography A,1992,609(1-2):69-81
[92]Wolf R.M.,Francotte E.,Lohmann D.Quantitative correlation between calculated molecular properties and retention of a series of structurally related racemates on cellulose triacetate[J].J.Chem.Soc.,Perkin Trans.2,1988:893-901
[93]Booth T.D.,Wainer I.W.Investigation of the enantioselective separations of a-alkylarylcarboxylic acids on an amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase using quantitative structure-enantioselective retention relationships Identification of a conformationally driven chiral recognition mechanism[J].Journal of Chromatography A,1996,737(2):157-169
[94]蒋华良,唐斌,陈凯先等.计算机辅助药物分子设计[J].上海:上海科技出版社,1996:
[95]仇缀百,万维,叶德泳等.药物设计学[M].北京:等教育出版社,1999.211-224
[96]Lipkowitz K.B.Theoretical studies of brush-type chiral stationary phases[J].Journal of Chromatography A,1994,666(1-2):493-503
[97]Lipkowitz K.B.Theoretical studies of type Ⅱ-Ⅴ chiral stationary phases[J].Journal of Chromatography A,1995,694(1):15-37
[98]Armstrong D.W.,Ward T.J.,Armstrong R.D.,et al.Separation of Drug Stereoisomers by the Formation of β-Cyclodextrin Inclusion Complexes,Science[J].science,1986,232:1132
[99]Armstrong R.D.,Ward T.J.,Pattabiraman N.,et al.Separation of tamoxifen geometric isomers and metabolites by bonded-phase β-cyclodextrin chromatography [J].Journal of Chromatography:Biomedicai Applications,1987,414:192-196
[100]Armstrong D.W.,Yang X.,Han S.M.,et al.Direct liquid chromatographic separation of racemates with an a-cyclodextrin bonded phase[J].Analytical Chemistry,1987,59(21):2594-2596
[101]Lipkowitz K.B.,Raghothama S.,Yang J.A.Enantioselective binding of tryptophan by a-cyclodextrin[J].Journal of the American Chemical Society,1992,114(5):1554-1562
[102]Kenny B.Lipkowitz C.M.S.Detailed experimental and theoretical analysis of chiral discrimination:Enantioselective binding of R/S methyl mandelate by β-cyclodextrin[J].Chirality,1996,8(4):341-350
[103]Kuroda Y.,Suzuki Y.,He J.,et al.Enantiorecognition of a new chiral selector,-cyclodextrin perphenylcarbamate,as studied by NMR spectroscopy and molecular energy calculation[J].J.Chem.Soc.,Perkin Trans.2,1995:1749-1759
[104]Durham D.G.,Hongxi L.Molecular modelling of the inclusion complexes between β-cyclodextrin and(R)/(S)-methylphenobarbitone and its application to HPLC[J].Chirality,1994,6(4):239-244
[105]David G Durham.Application of force field calculations to the prediction of chirally discriminating chromatographic behaviour for β-CDs[J].Chirality,1996,8(1):58-66
[106]Tesarov(?) E.,Gilar M.,Hobza P.,et al.Correlation between structure of dihydropyridine calcium antagonists and their retention behavior and enantioseparat ion on the β-cyclodextrin stationary phase in HPLC[J].Journal of High Resolution Chromatography,1995,18(9):597-601
[107]Copper C.L.,Davis J.B.,Cole R.O.,et al.Separations of derivatized amino acid enantiomers by cyclodextrin-modified capillary electrophoresis:Mechanistic and molecular modeling studies[J].Electrophoresis,1994,15(1):785-792
[108]K(o|¨)hler J.E.H.,Hohla M.,Richters M.,et al.Cyclodextrin Derivatives as Chiral Selectors investigation of the Interaction with(R,S)-Methyl-2-chloropropionate by Enantioselecfive Gas Chromatography,NMR Spectroscopy,and Molecular Dynamics Simulation[J].Angewandte Chemic International Edition in English,1992,31(3):319-320
[109]K(o|¨)hler J.E.H.,Hohla M.,Richters M.,et al.A Molecular-Dynamics Simulation of the Complex Formation between Methyl(R)/(S)-2-Chloropropionate and Heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin[J].Chemische Berichte,1994,127(1):119-126
[110]Vries N.K.d.,Coussens B.,Meier R.J.,et al.The separation of enantiomers on modified cyclodextrin columns:Measurements and molecular modeling[J].Journal of High Resolution Chromatography,1992,15(8):499-504
[111]Cozzini P.,Domiano P.,Musini P.C.,et al.Molecular modeling as a tool to discriminate between enantiomers resolved by derivatized cyclodextrins in gas chromatography[J].Journal of Inclusion Phenomena and Macrocyclic Chemistry,1996,26(4):295-302
[112]Kobor F.,Angermund K.,Schomburg G.Molecular modelling experiments on chiral recognition in GC with specially derivatized cyclodextrins as selectors[J].Journal of High Resolution Chromatography,1993,16(5):299-311
[113]Beier T.,H(o|¨)ltje H.-D.Modified cyclodextrins as chiral selectors:molecular modelling investigations on the enantioselective binding properties of heptakis(2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl)-β-cyclodextrin[J].Journal of Chromatography B:Biomedical Sciences and Applications,1998,708(1-2):1-20
[114]Lipkowitz K.B.,Pearl G.,Coner B.,et al.Explanation of Where and How Enantioselective Binding Takes Place on Permethylated β-Cyclodextrin,a Chiral Stationary Phase Used in Gas Chromatography[J].Journal of the American ChemicaiSociety,1997,119(3):600-610
[115]Kenny B.Lipkowitz B.C.,Michael A.Peterson,Antonio Morreale,.ENANTIO SELECTIVE BINDING IN GAS CHROMATOGRAPHY:A COMPUTATIONAL STUDY OF CHIRAL SELECTION BYPERMETHYL-β-CYCLODEXTRIN[J].Journal of Physical Organic Chemistry,1997,10(5):311-322
[116]Lipkowitz K.B.,Coner R.,Peterson M.A.Locating Regions of Maximum Chiral Discrimination:A Computational Study of Enantioselection on a Popular Chiral Stationary Phase Used in Chromatography[J].Journal of the American Chemical Society,1997,119(46):11269-11276
[117]Lipkowitz K.B.,Coner R.,Peterson M.A.,et al.The Principle of Maximum Chiral Discrimination:Chiral Recognition in Permethyl-β-cyclodextrin[J].The Journal of Organic Chemistry,1998,63(3):732-745
[118]Reinhardt R.,Richter M.,Mager P.,et al.Investigation of gas chromatographic interaction mechanism on permethylated cyclodextrins by molecular modelling[J]. Chromatographia,1996,43(3):187-194
[119]Black D.R.,Parker C.G.,Zimmerman S.S.,et al.Enantioselective binding of &agr;-pinene and of some cyclohexanetriol derivatives by cyclodextrin hosts:A molecular modeling study[J].Journal of Computational Chemistry,1996,17(8):931-939
[120]Manunza B.,Deiana S.,Pintore M.,et al.A molecular modeling study on the interaction between β-cyclodextrin and synthetic pyretroids[J].Carbohydrate Research,1997,300(1):89-93
[121]Kitae T.,Takashima H.,Kano K.Chiral Recognition of Phenylacetic Acid Derivatives by Aminated Cyclodextrins[J].Journal of Inclusion Phenomena and Macrocyclic Chemistry,1999,33(3):345-359
[122]Alvira E.,Garcfa J.I.,Mayoral J.A.Molecular modelling study for chiral separation of equol enantiomers by β-cyclodextrin[J].Chemical Physics,1999,240(1-2):101-108
[123]Li J.,Carr P.W.Extra-thermodynamic relationships in chromatography enthalpy-entropy compensation in gas chromatography[J].Journal of Chromatography A,1994,670(1-2):105-116
[124]Guillaume Y.C.,Guinchard C.New Statistical Approach to a Gas Chromatography Retention Model: Application to Dichlorophenol Isomers[J].The Journal of Physical Chemistry B,1997,101(41):8390-8394
[125]Stringham R.W.,Blackwell J.A.Factors That Control Successful Entropically Driven Chiral Separations in SFC and HPLC[J].Analytical Chemistry,1997,69(7):1414-1420
[126]王进防,周良模,刘学良等.分子烙印手性固定相分离过程热力学研究[J].高等学校化学学报,2000,6:930-933
[127]Koppenhoefer B.,Bayer E.Chiral recognition in the resolution of enantiomers by GLC[J].Chromatographia,1984,19(1):123-130
[128]周昕.,万宏.,庆瑜欧.2,6-O-二丁基-3-O-三氟乙酰基-γ-环糊精拆分一些氨基酸及分离机理探讨[J].分析化学,1994,22(6):560-564
[129]Aberg G.,MeCullough J.R.,Fang Y.reating urinary incontinence using (s)-deset hyloxybutynin.1997-10-14.
[130]Zhong Q.,Han X.,He L.,et al.Chromatographic evaluation of poly (trans-1,2-cyclohexanediyl-bis-acrylamide) as a chiral stationary phase for HPLC[J].J Chromatogr.A,2005,1066:55
[131]Holder N.L.,Chen T.M.,Matlinger A.C.Applications of ammonium trifluoroacetate as an additive for elution of chiral acids and bases from derivatized polysaccharide stationary phases[J].Chiralty,2005,17:S84
[132]Zhang Y.P.,Lee K.P.,Kim S.-H.Comparative study on the chiral separation of phenyl alcohols by capillary electrophoresis and liquid chromatography[J].Electrophoresis,2004,25:2711
[133]Schurig V.,Negura S.,Mayer S.Enantiomer separation on a Chirasil-Dex-poly-mer -coated stationary phase by conventional and micro-packed high-performance liquid chromatography[J].J Chromatogr.A,1996,755:299
[134]肖美添,黄雅燕,孟春等.扁桃酸甲酯对映体的毛细管电泳手性拆分[J].分析测试学报,2003,5(1):47
[135]黄雅燕,肖美添,石贤爱等.毛细管电泳法测定发酵液中的扁桃酸对映体含量[J].药物分析杂志,2004,24(5):460
[136]申河清,王清海,朱道乾等,七-(2,6-二戊基)-β-环糊精作为毛细管气相色谱固定相分离对映体的研究[J].分析测试学报,1998,17(1):45
[137]聂孟言,周良模,王清海等.扁桃酸及其类似物在全甲基环糊精固定相上的手性拆分[J].分析化学,2000,28(11):1366
[138]Koppenhoefer B.,Koch E.M.,Nicholson G.J.,et al.Chiral recognition of halo carboxylie acid amides studied by gas chromatography on chirasil-val[J].Journal of Chromatography A,1987,406:157-166
[139]Watabe K.Resolution of[alpha]-halogenocarboxylic acid amides on chiral N-lauroyl-[alpha]-(1-naphthyl)ethylamine Effect of the nature of the amide moiety of the solute[J].Journal of Chromatography,1987,399(Part 1):111-119
[140]施介华,徐秀珠,杨根生.反相高效液相色谱法拆分α-氯代丙酰替苯胺光学异构体[J].分析化学,2001,29(4):431-433
[141]McGachy N.T.,Grinberg N.,Variankaval N.Thermodynamic study of N-trifluoroacetyl-O-alkyl nipecotic acid ester enantiomers on diluted permethylated β-cyclodextrin stationary phase[J].Journal of Chromatography A,2005,1064(2):193-204
[142]Reijenga J.C.,Ingelse B.A.,Everaerts F.M.Thermodynamics of chiral selectivity in capillary electrophoresis:separation of ibuprofen enantiomers with b-cyclodextrin[J].J.Chromatogr.A.,,1997,792:371
[143]Maier N.M.,Franco P.,Lindner W.Separation of enantiomers:needs,challenges,perspectives[J].Journal of Chromatog.A,2001,906(1-2):3-33
[144]陈建荣,瞿超进.2-氯丙酸生产技术概况[J].河北工业科技,200219(2):49-51
[145]申桂英.2-氯丙酸[J].精细与专用化学品,2005,13(13):19-20,30
[146]施介华 金迪.,.李祥,周亮.2-氯丙酸及其酯的拆分研究进展[J].浙江工业大学学报,2006,34(5):502-508
[147]Chinchilla R.,Yus M.,Heumann A.Kinetic resolution of racemic carboxylic acids with homochiral alcohols and dicyclohexylcarbodiimide[J].Tetrahedron:Asymmetry,1991,2(2):101-104
[148]Overbeeke P.L.A.,Jongejan J.A.Enantioselectivity of Candida rugosa lipase in the hydrolysis of 2-chloropropionic acid methyl ester[J].Journal of Molecular Catalysis B:Enzymatic,2003,21(1-2):89-91
[149]施介华,金迪一种制备(S)-(-)-2-氯丙酸酯和(R)-(+)-2-氯丙酸的方法.2006.
[150]Watabe K.Resolution of a-halogenocarboxylic acid amides on chiral N-lauroyl-a-(1-naphthyl)ethylamine:Effect of the nature of the amide moiety of the solute[J].Journal of Chromatography A,1987,399:111-119
[151]李俊峰,都婷婷,兰先秋等.柱前衍生化高效液相色谱法准确测定2-氯丙酸的光学纯度[J].分析化学,2007,35(8):1195-1198
[152]Li W.Y.,Jin H.L.,Armstrong D.W.2,6-Di-O-pentyl-3-O-trifluoroacetyl cyclodextrin liquid stationary phases for capillary gas chromatographic separation of enantiomers[J].Journal of Chromatography A,1990,509(2):303-324
[153]Satoshi K.,Tsutomu S.,Yuichi K.,et al.Preparation of optically active compounds by optical resolution via extraction distillation 2005.
[154]Krug R.R.,Hunter W.G.,Grieger R.A.Enthalpy-entropy compensation.1.Some fundamental statistical problems associated with the analysis of van't Hoff and Arrhenius data[J].The Journal of Physical Chemistry,1976,80(21):2335-2341
[155]聂孟言,周良模,王清海等.α-溴丙酸甲酯与β-环糊精衍生物手性识别过程的模拟研究[J].化学学报,2001,59(2):268-273
[156]周英珍,王兴涌,张桂森等.环糊精及其衍生物在手性药物拆分中的应用[J].化学试剂,2006,28(10):590-592,59
[157]施介华,程向炜,周亮等.柱前衍生化法分离3-羟基丁酸乙酯光学异构体[J].分析化学,2007,35(5):714-718
[158]尤长城,赵彦利,刘育.竞争包结法研究β-环糊精及其两种衍生物对一些手性脂肪族客体分子的识别作用[J].高等学校化学学报,2001,22(2):218-222
[159]QI A.d.,LI L.,LIU Y.The Binding Ability and Inclusion Complexation Behavior of Curcumin with Naturalα-,β-,γ-Cyclodextrins and Organoselenium-Brid-ged Bis(β-cyclodextrin) s[J].Journal of Chinese Pharmaceutical Sciences,2003,12(1):15-20
[160]Yah C.,Xiu Z.,Li X.,et al.Molecular modeling study of β-cyclodextrin complexes with(+)-catechin and(-)-epicatechin[J].Journal of Molecular Graphics and Modelling,2007,26(2):420-428
[161]施介华,江峰,王桂林等.酯在聚硅氧烷类固定相上的色谱保留机理研究[J].浙江工业大学学报,2004,32(4):418-422
[162]Lipkowitz K.B.Applications of Computational Chemistry to the Study of Cyclodextrins[J].Chemical Reviews,1998,98(5):1829-1874
[163]Dodziuk H.,Lukin O.,Nowinski K.S.Molecular mechanics calculations of molecular and chiral recognition by cyclodextrins.Is it reliable? The selective complexation of decalins by β-cyclodextrin[J].Journal of Molecular Structure:THEOCHEM,2000,503(3):221-230
[164]Madrid J.M.,Pozuelo J.,Mendicuti F.,et al.Molecular Mechanics Study of the Inclusion Complexes of 2-Methyl Naphthoate with a-and β-Cyclodextrins[J].Journal of Colloid and Interface Science,1997,193(1):112-120
[165]Ding H.,Chao J.,Zhang G.,et al.Preparation and spectral investigation on inclusion complex of[beta]-cyclodextrin with rutin[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2003,59(14):3421-3429
[166]Halgren T.A.MMFF Ⅶ.Characterization of MMFF94,MMFF94s,and other widely available force fields for conformational energies and for intermolecularinteraction energies and geometries[J].Journal of Computational Chemistry,1999,20(7):730-748
[167]Kitagawa M.,Hoshi H.,Sakurai M.,et al.The large dipole moment of cyclomaltohexaose and its role in determining the guest orientation in inclusion complexes[J].Carbohydrate Research,1987,163(1):c1-c3
[168]Huang M.J.,Watts J.D.,Bodor N.Theoretical studies of inclusion complexes of β-cyclodextrin with methylated benzoic acids[J].International Journal of Quantum Chemistry,1997,64(6):711-719
[169]Huang M.-J.,Watts J.D.,Bodor N.Theoretical studies of inclusion complexes of β-cyclodextrin with methylated benzoic acids[J].International Journal of Quantum Chemistry,1997,64(6):711-719
[170]Song K.S.,Hou C.R.,Liu L.,et al.A quantum-chemical study on the molecular recognition of β-cyclodextrin with ground and excited xanthones[J].Journal of Photochemistry and Photobiology A:Chemistry,2001,139(2-3):105-109
[171]Cao Y.,Xiao X.,Ji S.,et al.Study of the inclusion processes of styrene and a-methyl-styrene in β-cyclodextrin[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2004,60(4):815-820
[172]Steiner T.,Koellner G.Crystalline.β-Cyclodextrin Hydrate at Various Humidities:Fast,Continuous,and Reversible Dehydration Studied by X-ray Diffraction[J].Journal of the American Chemical Society,1994,116(12):5122-5128
[173]Frisch M.J.,Trucks G.W.,Schlegel H.B.,et al.Gaussian 03,Gaussian,Inc:Pittsburgh PA,2003.
[174]Liu L.,Li X.S.,Guo Q.X.Orientation conversion in the complexation of a-cyclodextrin with 4-fluorophenol:a PM3 quantum chemical study[J].Journal of Molecular Structure:THEOCHEM,2000,530(1-2):31-37
[175]Saenger W.,Noltemeyer M.,Manor P.C.,et al."Induced-fit"-type complex formation of the model enzyme a-cyclodextrin[J].Bioorganic Chemistry,1976,5(2):187-195
[176]Liu L.,Li X.S.,Song K.S.,et al.PM3 studies on the complexation of a-cyclodextrin with benzaldehyde and acetophenone[J].Journal of Molecular Structure:THEOCHEM,2000,531(1-3):127-134
[177]Alvira E.,Mayoral J.A.,Garcfa J.I.Molecular modelling study of β-cyclodextrin inclusion complexes[J].Chemical Physics Letters,1997,271(1-3):178-184
[178]Kenny B.Lipkowitz B.C.,Michael A.Peterson,Antonio Morreale,.ENANTIO SELECTIVE BINDING IN GAS CHROMATOGRAPHY:A COMPUTATIONAL STUDY OF CHIRAL SELECTION BYPERMETHYL-β-CYCLODEXTRIN[J].Journal of Physical Organic Chemistry,1997,10(5):311-322
[179]缪方明,宿秀梅,徐秀丽.β-环糊精包合物的量子化学计算[J].计算机与应用化学,2002,19(3):315-319
[180]梁文杰.众志成城的氢键 化学中的小矮人[J].CHEMISTRY THE CHINESE CHEM.SOC.,,2004,62(1):
[181]江峰,施介华,严巍等.分子模型及其在手性识别机理研究上的应用[J].分析化学,2004,32(11):1550-1555
[182]高如瑜,王荷芳.QSERRs方法及其在色谱手性识别机理研究中的应用[J].有机化学,1999,19(2):135-140
[183]欧阳亮,何谷,郭丽.一类新型N型钙通道阻滞剂的比较定量构效关系研究[J].化学学报,2006,64:1379-1384
[184]施介华,江峰,严巍等.烃类化合物在不同色谱柱上的定量结构-保留相关性研究[J].分析化学,2005,33(2):181-186
[185]曾小兰,柳红霞,刘红艳.多氯联苯醚的结构参数和热力学性质的密度泛函理论研究[J].化学学报,2007,65:1797
[186]黄君珉,陈慧,高如瑜等.衍生化环糊精键合固定相色谱保留和手性识别机理的研究(Ⅱ)[J].高等学校化学学报,2001,22(11):1838-1842
[187]陈慧,吕宪禹,黄君珉等.衍生化环糊精键合固定相色谱保留和手性识别机理的研究(Ⅰ)[J].高等学校化学学报,2000,21(4):562-565
[188]Suzuki T.,Timofei S.,Iuoras B.E.,et al.Quantitative structure-enantioselective retention relationships for chromatographic separation of arylalkylcarbinols on Pirkle type chiral stationary phases[J].Journal of Chromatography A,2001,922(1-2):13-23
[189]陈娟娟,张大同,沈报春等.D,L-α-氨基酸对映体在冠醚手性柱上的分离[J].分析化学,2006,34(11):1535-1540
[190]Machida Y.,Nishi H.,Nakamura K.,et al.Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether[J].Journal of Chromatography A,1998,805(1-2):85-92
[191]Hyun M.H.,Jin J.S.,Koo H.J.,et al.Liquid chromatographic resolution of racemic amines and amino alcohols on a chiral stationary phase derived from crown ether[J].Journal of Chromatography A,1999,837(1-2):75-82
[192]Hyun M.H.,Han S.C.,Lipshutz B.H.,et al.New chiral crown ether stationary phase for the liquid chromatographic resolution of a-amino acid enantiomers[J].Journal of Chromatography A,2001,910(2):359-365
[193]Sousa L.R.,Sogah G.D.Y.,Hoffman D.H.,et al.Host-guest complexation.12.Total optical resolution of amine and amino ester salts by chromatography[J].Journal of the American Chemical Society,1978,100(14):4569-4576
[194]Matlin S.A.,Tiritan M.E.,Crawford A.J.,et al.HPLC with carbohydrate carbamate chiral phases:Influence of chiral phase structure on enantioselectivity[J].Chirality,1994,6(2):135-140
[195]王鹏.定量构效关系及研究方法[M].哈尔滨工业大学出版社,2004.
[196]Azzaoui K.,Morin-Allory L.Comparison and quantification of chromatographic retention mechanisms on three stationary phases using structure-retention relation ships[J].Chromatographia,1996,42(7):389-395