环糊精型手性固定相的制备及色谱拆分与保留机理研究
|
摘要
本论文主要包括以下几方面:
1.简述了手性物质拆分的重要性、色谱拆分技术和环糊精及其衍生物手性固定相的研究进展。
2.分别用3-缩水甘油基丙基三甲氧基硅烷(KH-560)和3-异氰酸丙基三乙氧基硅烷(IPTS)作为偶联剂,合成了β-环糊精键合手性固定相。通过比较,以KH-560为偶联剂合成的β-环糊精键合手性固定相具有键合量大,柱效高,稳定性好等优点,且对盐酸四咪唑以及安息香类化合物具有较好的拆分能力。
3.制备了羟丙基-β-环糊精键合手性固定相。比较分析了羟丙基-β-环糊精键合手性固定相和β-环糊精键合手性固定相对氢化安息香、安息香和α-苯乙醇拆分的影响。结果表明,在所有流动相中,氢化安息香和安息香都获得了拆分,而α-苯乙醇未得到拆分。硼酸缓冲盐对氢化安息香拆分的影响很大。结合线性溶剂强度(LSS)模型和计量置换理论(SDM-R)对手性识别机理进行了探讨。
4.利用R-1-苯基乙基异氰酸酯对β-环糊精键合固定相进行衍生,合成了不同取代度的R-1-苯基乙基氨基甲酸酯-β-环糊精键合手性固定相。填充后在反相条件下考察对氢化安息香、安息香和α-苯乙醇的手性拆分,探讨了流动相中乙腈含量、缓冲盐类型对手性拆分的影响。结果表明,乙腈作为流动相的有机添加剂时,色谱峰形对称,基线噪音小,柱效高,化合物出峰时间短。氢化安息香获得了基线分离,分离因子可达1.214,而安息香得到了部分分离,α-苯乙醇未能拆开。结合LSS模型和SDM-R模型对手性拆分及色谱保留机理进行了探讨,认为水分子和乙腈分子一起参与了溶质的置换。
5.制备了3, 5-二甲基苯基氨基甲酸酯-β-环糊精键合手性固定相。在正相和反相两种模式下,考察了该固定相的手性拆分性能。
Following aspects were represented in this study:
1. The importance of chiral separation, the main chiral chromatographic separation techniques and the recent development of cyclodextrin-based chiral stationary phases were briefly discussed.
2. The synthesis and evaluation ofβ-cyclodextrin (β-CD) bonded chiral stationary phases (CSPs) with 3-glycidoxyproryl-trimethoxysilane (KH-560) or 3-isocyanatopropyltriethoxy- silane (IPTS) for the enantioseparation of various chiral analytes by HPLC were presented. By comparison, the former was deemed to have higher bonded amount, higher enantiosparation ability and better stability.
3. A hydroxypropyl-β-cyclodextrin (HP-β-CD) bonded chiral stationary phase (CSP) was prepared. Comparative evaluations of these two CSPs for the enantioseparation of hydrobenzoin, benzoin andα-phenethyl alcohol by HPLC were presented. The effects of buffer composition in the mobile phase on the retention and enantioseparation were investigated. The borate buffer had a significant influence on the retention and enantioseparation of hydrobenzoin. Linear solvent strength (LSS) retention model was used to fit the chromatographic data. Good linearity existed between the common logarithm of retention factor (k) and the volume fraction of organic modifier (φ). Another retention model, stoichiometric displacement theory for retention (SDT-R), was also tried to fit the chromatographic data. The results showed that not only acetonitrile, but also water molecules participated in the displacing process of the solute.
4. R-1-Phenylethylcarbamoylatedβ-CD-CSP was prepared from R-1-Phenylethyl isocyanate andβ-cyclodextrin bonded CSP. The obtained CSP was packed by slurrying method. Then enantioseparations of hydrobenzoin, benzoin andα-phenethyl alcohol were evaluated under the reversed mode. The effects of acetonitrile amount and buffer type on the retention and enantioseparation were investigated. Hydrobenzoin obtained baseline separation, and the separation factor could reach 1.214. Benzoin obtained partial enantioseparation, and α-phenethyl alcohol could not be separated wholly. Chiral recognition mechanism was studied with the LSS and SDM-R models. Water molecules and acetonitrile molecules were considered to participate in the displacing process.
5. Two 3, 5-dimethylphenyl carbamoylatedβ-cyclodextrin stationary phases were prepared in the different solvents. Then the enantioseparation ability of the CSPs was evaluated under normal-phase or reverse-phase condition by HPLC.
1.简述了手性物质拆分的重要性、色谱拆分技术和环糊精及其衍生物手性固定相的研究进展。
2.分别用3-缩水甘油基丙基三甲氧基硅烷(KH-560)和3-异氰酸丙基三乙氧基硅烷(IPTS)作为偶联剂,合成了β-环糊精键合手性固定相。通过比较,以KH-560为偶联剂合成的β-环糊精键合手性固定相具有键合量大,柱效高,稳定性好等优点,且对盐酸四咪唑以及安息香类化合物具有较好的拆分能力。
3.制备了羟丙基-β-环糊精键合手性固定相。比较分析了羟丙基-β-环糊精键合手性固定相和β-环糊精键合手性固定相对氢化安息香、安息香和α-苯乙醇拆分的影响。结果表明,在所有流动相中,氢化安息香和安息香都获得了拆分,而α-苯乙醇未得到拆分。硼酸缓冲盐对氢化安息香拆分的影响很大。结合线性溶剂强度(LSS)模型和计量置换理论(SDM-R)对手性识别机理进行了探讨。
4.利用R-1-苯基乙基异氰酸酯对β-环糊精键合固定相进行衍生,合成了不同取代度的R-1-苯基乙基氨基甲酸酯-β-环糊精键合手性固定相。填充后在反相条件下考察对氢化安息香、安息香和α-苯乙醇的手性拆分,探讨了流动相中乙腈含量、缓冲盐类型对手性拆分的影响。结果表明,乙腈作为流动相的有机添加剂时,色谱峰形对称,基线噪音小,柱效高,化合物出峰时间短。氢化安息香获得了基线分离,分离因子可达1.214,而安息香得到了部分分离,α-苯乙醇未能拆开。结合LSS模型和SDM-R模型对手性拆分及色谱保留机理进行了探讨,认为水分子和乙腈分子一起参与了溶质的置换。
5.制备了3, 5-二甲基苯基氨基甲酸酯-β-环糊精键合手性固定相。在正相和反相两种模式下,考察了该固定相的手性拆分性能。
Following aspects were represented in this study:
1. The importance of chiral separation, the main chiral chromatographic separation techniques and the recent development of cyclodextrin-based chiral stationary phases were briefly discussed.
2. The synthesis and evaluation ofβ-cyclodextrin (β-CD) bonded chiral stationary phases (CSPs) with 3-glycidoxyproryl-trimethoxysilane (KH-560) or 3-isocyanatopropyltriethoxy- silane (IPTS) for the enantioseparation of various chiral analytes by HPLC were presented. By comparison, the former was deemed to have higher bonded amount, higher enantiosparation ability and better stability.
3. A hydroxypropyl-β-cyclodextrin (HP-β-CD) bonded chiral stationary phase (CSP) was prepared. Comparative evaluations of these two CSPs for the enantioseparation of hydrobenzoin, benzoin andα-phenethyl alcohol by HPLC were presented. The effects of buffer composition in the mobile phase on the retention and enantioseparation were investigated. The borate buffer had a significant influence on the retention and enantioseparation of hydrobenzoin. Linear solvent strength (LSS) retention model was used to fit the chromatographic data. Good linearity existed between the common logarithm of retention factor (k) and the volume fraction of organic modifier (φ). Another retention model, stoichiometric displacement theory for retention (SDT-R), was also tried to fit the chromatographic data. The results showed that not only acetonitrile, but also water molecules participated in the displacing process of the solute.
4. R-1-Phenylethylcarbamoylatedβ-CD-CSP was prepared from R-1-Phenylethyl isocyanate andβ-cyclodextrin bonded CSP. The obtained CSP was packed by slurrying method. Then enantioseparations of hydrobenzoin, benzoin andα-phenethyl alcohol were evaluated under the reversed mode. The effects of acetonitrile amount and buffer type on the retention and enantioseparation were investigated. Hydrobenzoin obtained baseline separation, and the separation factor could reach 1.214. Benzoin obtained partial enantioseparation, and α-phenethyl alcohol could not be separated wholly. Chiral recognition mechanism was studied with the LSS and SDM-R models. Water molecules and acetonitrile molecules were considered to participate in the displacing process.
5. Two 3, 5-dimethylphenyl carbamoylatedβ-cyclodextrin stationary phases were prepared in the different solvents. Then the enantioseparation ability of the CSPs was evaluated under normal-phase or reverse-phase condition by HPLC.
引文
[1] Raval R. Mirrors in Flatland [J]. Nature, 2003, 425(6957): 463–464.
[2] Stephens T D, Bunde C J, Fillmore B J. Mechanism of action in thalidomide teratogenesis [J]. Biochem. Pharmacol., 2000, 59(12): 1489–1499.
[3]张玮,尚平,姚军.手性药物与手性分离技术[J].河北化工, 2004, 27(5): 12–14.
[4]宫丽,卞俊.手性药物的药理学立体选择性[J].国外医学·药学分册, 2007, 34(2):123–126.
[5] Patel R N. Biocatalytic Synthesis of Chiral Pharmaceutical Intermediates [J]. Food Technol. Biotechnol, 2004, 42(4): 305–325.
[6] Liu M, Li L S, Da S L, Feng Y Q. High performance liquid chromatography with cyclodextrin and calixarene macrocycle bonded silica stationary phases for separation of steroids [J]. Talanta, 2005, 66(2): 479–486.
[7] Lin C H, Chen C Y, Chang S W, Wu J C, Lin C E. Use ofβ-cyclodextrin bonded phase with s-triazine moiety in the spacer for separation of aromatic carboxylic acid isomers by high-performance liquid chromatography [J]. Anal. Chim. Acta, 2006, 576(1): 84–90.
[8] Campos-Candel A, Llobat-Estellés M, Mauri-Aucejo A. Comparative evaluation of liquid chromatography versus gas chromatography using aβ-cyclodextrin stationary phase for the determination of BTEX in occupational environments [J]. Talanta, 2009, 78 () 1286–1292.
[9] Schleuder M, Durrbeck A, Jira T. The Influence of Cyclodextrin on the Stability of Cephalotin and Aztreomam in Aqueous Slution [J]. Pharmazie, 1998, 53 (6): 381–386.
[10]杨欣欣,陈国文,赵士贵,王峰,王旭波.环糊精及其衍生物在气相色谱中的应用进展[J].山东化工, 2007, 36(4): 11–13.
[11]李晓霞,王佳.环糊精类固定相在气相色谱中的应用[J].延安大学学报(自然科学版), 2004, 23(2): 64–69.
[12]尹明明.环糊精类气谱手性固定相的合成及其手性分离性能的研究[D].北京:中国农业大学, 2006: 4–6.
[13]李清华.气相色谱法测定羟丙基-β-环糊精平均取代度[J].应用化工, 2009, 28(1): 139–141.
[14]陶旦妮,史雪岩,顾峻岭,傅若农.环糊精衍生物固定相毛细管气相色谱法分离甲酚位置异构体[J].分析化学, 2001, 29(10): 1150–1153.
[15] Krup?ík J, MájekováM, Májek P, Hrouzek J, Benicka E, Onuska F, Sandra P, Zeeuw J. On the interconversion energy barriers obtained for atropisomers of some polychlorinated biphenyls by AM1 semiempirical quantum chemistry method and gas chromatography on a modified cyclodextrin stationary phase [J]. Anal. chem., 1995, 352(7-8): 696–698.
[16] Abe I, Nishiyama T, Nakahara T, Frank H. Gas chromatographic enantiomer separation of pharmaceuticals on capillary columns coated with novel chiral polysiloxanes [J]. J. Chromatogr. A, 1995, 694(1): 237–243.
[17] Bicchi C, D’Amato A, Rubiolo P. cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oilmaroma and flavours fields [J]. J. Chromatogr. A, 1999, 843 (1-2)99–121.
[18] Quattrini F, Biressi G, Juza M, Mazzotti M, Fuganti C, Morbidelli M. Enantiomer separation of a-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases [J]. J. Chromatogra. A, 1999, 865(1-2): 201–210.
[19] Schurig V. Separation of enantiomers by gas chromatography [J]. J. Chromatogra. A, 2001, 906(1-2): 275–299.
[20] K?nigW A, Lutz S, Wenz G, Bey E. Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part II: Heptakis (3-O-acetyl-2, 6-di-O-pentyl)-?-cyclodextrin [J]. J. High. Resolut. Chromatogr., 1988, 11(7): 506–509.
[21] Shi X, Guo H, Wang M. Enantioseparation of chiral epoxides using four new cyclodextrin derivatives as chiral stationary phases of capillary gas chromatography [J]. Anal. Chim. Acta, 2005, 553(1-2) 43–49.
[22] Shi X, Liang P, Gao X. The capillary gas chromatographic properties of fourβ-cyclodextrin derivatives with allyl groups or propyl groups on 3-position or 6-position ofβ-cyclodextrin [J]. Anal. Chim. Acta, 2005, 548(1-2): 86–94.
[23] Mallmann A S, Ethur E M, Silva U F, Dalcol I I, Morel A F. Synthesis and Chromatographic Evaluation of the New Phase Heptakis (3-O-pentafluoropropionyl- 2,6-di-O-pentyl)-β-cyclodextrin [J]. J. Braz. Chem. Soc., 2010, 21(10): 2005–2011.
[24] McGachy N T, Grinberg N, Variankaval N. Thermodynamic study of N-trifluoroacetyl-O-alkylnipecotic acid ester enantiomers on diluted permethylated- cyclodextrin stationary phase [J]. J. Chromatogra. A, 2005, 1064(2): 193–204.
[25]周美杨,凌云,申刚义,杨新玲.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能[J].高等学校化学学报, 2008, 29(3): 493–497.
[26]申刚义,崔箭,杨新玲,周美杨,凌云.一种吡啶杂环β-环糊精固定相的制备及其气相色谱分离性能[J].理化检验-化学分册, 2009, 45(2):222–224.
[27]朱小波,陈福良,尹明明.全烷基化β-环糊精混合固定相上一些取代苯类手性化合物的气相色谱分离研究[J]. 2009, 28(4):409-413.
[28] Huang K, Armstrong D W, Forro E, Fulop F, Peter A. Separation of Enantiomers and Control of Elution Order ofβ-Lactams by GC Using Cyclodextrin-Based Chiral StationaryPhases [J]. Chromatographia, 2009, 69(3-4): 331–337.
[29] Akapo S, McCrea C, Gupta J, Roach M, Skinner W. Chiral HPLC analysis of formoterol stereoisomers and thermodynamic study of their interconversion in aqueous pharmaceutical formulations [J]. J. Pharmaceutical and Biomedical Anal., 2009, 49(3): 632–637.
[30] Al-Majed A A. A direct HPLC method for the resolution and quantitation of the R-(?)- and S-(+)-enantiomers of vigabatrin (γ-vinyl-GABA) in pharmaceutical dosage forms using teicoplanin aglycone chiral stationary phase[J] . J. Pharm. Biomed. Anal., 2009, 50(1): 96–99.
[31] Easton C, Lincoln S. Chiral discrimination by modified cyclodextrins [J]. Chem. Soc. Rev., 1996, 25(1): 163–170.
[32] Armstrong D W, DeMond W, Cyclodextrin bonded phases for the liquid chromatographic separation of optical, geometrical, and structural isomers [J]. J. Chromatogr. Sci., 1984, 22(9): 411–415.
[33]阮源萍,张雪曼,陈安齐. 2,6-二-O-烷基-β-环糊精涂渍手性固定相分离联萘酚类对映异构体[J].厦门大学学报(自然科学版), 2004, 43(3): 8–92.
[34]曾苏.高效液相色谱手性流动相添加剂法分离药物对映体[J].色谱, 1995, 13(1): 21–25.
[35] Toyohide T, Homare A, Daido S. Enantiomeric resolution of dansyl amino acids by micro high-performance liquid chromatography withβ-cyclodextrin inclusion complexes [J]. J. Chromatogr., 1986, 357: 409–415.
[36]姚彤炜,曾苏,丁海青.环糊精类手性流动相添加剂及其在药物分析中的应用[J].色谱, 1996,14(2): 106–110.
[37]李桦,胡先明,谢颖峰.高效液相色谱手性流动相添加剂分离肾上腺素类对映体[J].色谱, 1998, 16(5): 424–426.
[38] Schmid M G, H?rringer B, Gübitz G. Chiral Resolution of RR,SS-Hydrobenzoin by Liquid Chromatography Using Borate-Cyclodextrin Complexation [J]. J. High Resol. Chromatogr.1998, 21(7): 414–416.
[39]宁凤容,黄可龙,焦飞鹏. HP-β-CD手性流动相HPLC法拆分萘普生对映体的色谱保留机制和拆分机理研究[J].化学通报, 2006, (6): 425–429.
[40]周采菊,刘瑛. HPLC手性流动相添加剂法拆分马来酸氨氯地平[J].中国现代应用药学, 2009, 26(9): 757–759.
[41] Ma S, Shen S, Haddad N, Tang W, Wang J, Lee H, Yee N, Senanayake C, Grinberg N. Chromatographic and spectroscopic studies on the chiral recognition of sulfatedβ-cyclodextrin as chiral mobile phase additive: Enantiomeric separation of a chiral amine [J]. J.Chromatogra. A, 2009, 216(8): 1232–1240.
[42] Weng W, Wang Q H, Yao B X, Zeng Q L. Enantioseparation of amino acid derivatives on an immobilized network polymer derived from L-tartaric acid [J]. J. Chromatogr. A, 2004, 1042(1-2): 81–87 [[43]翁文,林敏,钟艺聪. L-酒石酸型固定相对映分离氨基酸衍生物[J].分析化学, 2004, 32(2): 213–216.
[44]唐琴.高效液相色谱手性固定相法拆分药物对映体研究[D].四川:四川大学. 2004: 15–17.
[45] Weng W, Zeng Q L, Wang Q H. Influence of mobile phase composition on the apparent thermodynamic characteristics in the high performance liquid chromatographic enantioseparation on a tartaric acid derivatized network polymer [J]. Chromatographia, 2005, 61(11-12): 561–566.
[46]翁文,姚碧霞,陈秀琴,陈友遵,林文士,曾庆乐.液相色谱手性拆分机理的热力学方法研究[J]化学进展, 2006, 18(7/8): 1056–1064.
[47] Weng W, Zeng Q L, Yao B X. Enantioseparation of Amino Acid Derivatives with a Cellulose-Based Stationary Phase [J]. Chromatographia, 2006, 64(7-8): 463–467.
[48]翁文,林文士,姚碧霞.纤维素型手性固定相拆分亚砜系列化合物[J].分析化学, 2006, 34(6): 805–808.
[49]翁文,范文静,朱钦.联萘系列化合物在甘氨酸型手性固定相上的拆分[J].分析测试学报, 2008, 27(7):721–724.
[50] Weng W, Zhan F P, Fu J, Li T, Chen X,.Huang X. Enantioseparation of binaphthol and its derivatives on cellulose tris (3, 5-dimethylphenyl carbamate) [J]. Chromatographia, 2008, 67(1-2): 119–123.
[51]陈立仁.液相色谱手性分离[M].北京:科学出版社, 2006: 35-80.
[52] Malik A, Jinno K. Retention Behaviour of Aromatic Compounds in Liquid Chromatography and Supercritical Fluid Chromatography with Coarse-Particles of Bondedβ-Cyclodextrin Stationary Phase[J]. Chromatographia, 1991, 31(11/12): 561–568.
[53] Shen Y, Chen Z, Owen N L, Li W, Bradshaw J S, Lee M L. Cyclodextrin polymer encapsulated particles for supercritical fluid chromatography [J]. J. Microcolumn Sep., 1996, 8(4): 249–257.
[54] Wang R Q, Ong T T, Ng S C. Synthesis of cationicβ-cyclodextrin derivatives and their applications as chiral stationary phases for high-performance liquid chromatography and supercritical fluid chromatography [J]. J. Chromatogra. A, 2008, 1203(2): 185–192.
[55]申丽红.超临界介质中卤代离子液体的合成及其在β-环糊精改性中的应用[D].西安:陕西师范大学, 2008: 17–19.
[56] Aumatell A, Guttman A. Ultra-fast chiral separation of basic drugs by capillary electrophoresis [J]. J. Chromatogr. A, 1995, 717(1-2): 22–234.
[57] Stalcup A M, Gahm K H. A sulfated cyclodextrin chiral stationary phase for high-performance liquid chromatography[J]. Anal Chem, 1996, 68(8): 1360-1368
[58] Gubitz G, Schmid M G. Chiral separation principles in capillary electrophoresis [J]. J. Chromatogr. A, 1997, 792(1-2): 179–225.
[59] Schmid M G, Wirnsberger K, Jira T, Bunke A, Gubitz G. Capillary Electrophoretic Chiral Resolution of Vicinal Diols by Complexation With Borate and Cyclodextrin: Comparative Studies on Different Cyclodextrin Derivatives [J]. Chirality, 1997, 9(2): 153–156.
[60] Stádberg O, Hedeland M, Pettersson C, Westerlund D. The Effect of Conductivity Tuning in Chiral Separations by CE: Using Hydroxypropyl-13- Cyclodextrin in Combination with Tetraalkylammonium lons [J]. Chromatographia, 1998, 48(5-6): 415–421.
[61] Zhou A, Lv X, Xie Y, Yan C, Gao R. Chromatographic evaluation of perphenylcarbamoylatedβ-cyclodextrin bonded stationary phase for micro-high performance liquid chromatography and pressurized capillary electrochromatography [J]. Anal. Chim. Acta, 2005, 547(2): 158–164.
[62]马剑茵.手性药物的色谱分离方法[J].中国医药工业杂志, 2002, 33(4): 199–202.
[63]朱晓峰,林炳承.毛细管区带电泳法拆分手性药物萘普生和氟联苯丙酸[J].色谱, 2000, 18(1): 70–72.
[64]史雪岩,梁沛,宋敦伦,高希武.聚合-β-环糊精作手性添加剂的毛细管电泳法分离4种光学活性农药中间体[J].分析化学, 2004, 32(11): 1421–1425.
[65] Wang J, Yuan Q, Evans D G, Yang L, Zheng G, Sun W. Enantioselective separation of phenylglycidates by capillary electrophoresis employing sulfatedβ-cyclodextrin as chiral selector [J]. J. Chromatogra. B, 2007, 850(1-2): 560–563.
[66]夏陈,陈志涛,夏之宁.基于非手性离子液体的毛细管电泳法拆分3种手性药物[J].色谱, 2008, 26(6): 677–681.
[67]郑志侠,汪家权,程红,肖莆.基于环糊精手性选择剂的几种手性药物对映体的毛细管电泳拆分[J].化学研究, 2010, 21(1): 76–79.
[68] Zhu H, Wu E, Chen, J Jang Y S, Kang W, Choi J K, Lee W, Kang J S. Reverse migration order of sibutramine enantiomers as a function of cyclodextrin concentration in capillary electrophoresis [J]. J. Pharm. Biomed. Anal., 2011, 54(5): 1007–1012.
[69] Zaidi S A, Lee S M, Cheong W J. Open tubular capillary columns with basic templates made by the generalized preparation protocol in capillary electrochromatography chiral separation and template structural effects on chiral separation capability [J]. J. Chromatogra. A, 2011, 1218 (9): 1291–1299.
[70] Szejtli J. Cyclodextrin and their inclusion complexes [M]. Budapest: Akademiai Kiado, 1982:277–289.
[71] Breslow R, Zhang X, Xu R, Maletic M, Merger R. Selective catalytic oxidation of substrates That Bind to Metalloporphyrin Enzyme Mimics Carrying Two or Four Cyclodextrin Groups and Related Metallosalens [J]. J. Am. Chem. Soc., 1996, 118(46): 11678–11679.
[72]张雪飞.环糊精的研究进展及其应用[J].内蒙古民族大学学报, 2010, 16(5):31–32.
[73]廖才智.β-环糊精的应用研究进展[J].化工科技, 2010, 18(5): 69–72.
[74]凌云,傅若农.环糊精衍生物固定相在色谱分离光活性化合物中的应用进展[J].化学试剂, 1996, 18(1): 19–24.
[75]张纪贵,郝爱友.β-环糊精固定相在色谱中的应用及发展趋势[J].化学研究与应用, 2003, 15(3): 303–306.
[76] Thuaud N, Sébille B, Deratani A, Lelièvre G. Retention behavior and chiral recognition ofβ-cyclodextrin-derivative polymer adsorbed on silica for warfarin, structurally related compounds and Dns-amino acids [J]. J. Chromatogr., 1991, 555(1-2): 53–64.
[77] Thuaud N, Sébille B, Deratani A, P?pping B, Pellet C. Enantiomer separations with chromatographic supports based onβ-cyclodextrin polymers immobilized on porous silica: role of the polymer structure in separating ability [J]. Chromatographia, 1993, 36(23): 373–380.
[78] Crini G, Morcellet M, Torri G. HPLC of structural isomers with cyclodextrin-poly (vinylamine)-coated silica columns, Part I: Synthesis and characterization of cyclodextrin-bonded stationary phases by NMR solid state [J]. J. Chromatogr. Sci., 1996, 34(11): 477–484.
[79] Crini G, Morcellet M, Torri G. HPLC of structural isomers using cyclodextrin-poly (vinylamine)-coated silica columns, Part II: Retention behavior and separation [J]. J. Chromatogr. Sci., 1996, 34(11): 485–494.
[80] Thuaud N, G Lelièvre, Deratani A, Sébille B. Preparation of chiral stationary phases by graftingβ-CD derivatives on polyvinylimidazole coated silica [J]. Eur. Polym. J., 1997, 33(7): 1015–1020.
[81] Ong T T, Wang R Q, Muderawan I W, Ng S C. Synthesis and application of mono-6-(3-methylimidazolium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride as chiral stationary phases for high-performance liquid chromatography and supercritical fluid chromatography[J]. J. Chromatogra. A, 2008, 1182 (1): 136–140.
[82] Yin M M, Zhu X B, Liu Y L, Zhong J C, Chen F L. Synthesis of heptakis(2,3,6-tri-O-methoxymethyl)-β-cyclodextrin and its application in gas chromatography [J]. Chinese J. Chromatogra., 2011, 29(01): 91–94.
[83]都振华,王莉晶. N-叔丁氧羰基-L-丙氨酸衍生化环糊精键合硅胶固定相的合成与性能研究[J].工程技术, 2009, (22): 31–32.
[84] Lai X H, Ng S C. Convenient synthesis of mono (6A-N-allylamino-6A-deoxy)-permethylatedβ-cyclodextrin: a promising chiral selector for an HPLC chiral stationary phase [J]. Tetrahedr. Lett. 2004, 45(23): 4469–4472.
[85]罗爱芹,刘立文,戴荣继,郝建薇,张金专,方敏. 2, 6-二-O-苄基-β-环糊精键合硅胶固定相的合成与色谱性能[J].北京理工大学学报, 2005, 25(1): 87–90.
[86] Franco E, Senso A, Olivems L, Minguillon C. Covalently bonded polysaccharide derivatives as chiral stationaryphases in high-performance liquid chromatography [J]. J. Chromatogr. 2001, 906(1-2): 155–170.
[87] Muderawan I W, Ong T T, Ng S C. Urea bonded cyclodextrin derivatives onto silica for chiral HPLC[J]. J. Sep. Sci., 2006, 29(12): 1849–1871.
[88]冯钰锜,达世禄.甘氨酸衍生化β-环糊精键合硅胶液相色谱固定相的合成与评价[J].色谱, 2000, 18(3): 224–228.
[89]杨少宁,罗爱芹,侯爱军. 3, 5-二硝基苯甲酰化β-环糊精键合硅胶手性固定相的合成及高效液相色谱中的手性分离研究[J].分析科学学报, 2008, 24(5): 615–617.
[90] Thamarai C S K, Yong E L, Gong Y. Preparation and evaluation of calix[4]arene-cappedβ-cyclodextrin-bonded silica particles as chiral stationary phase for high-performance liquid chromatography [J]. J. Chromatogra. A, 2008, 1203(1) 54–58.
[91]陈立仁.液相色谱手性分离[M].北京:科学出版社, 2006: 107–108.
[92]黄天宝,吴邦桂,龙远德,旷昌渝,周竞先.β-CD键合固定相的制备和评价[J].分析化学, 1991, 19(11): 1257–1260.
[93]龚银汉,董亚琼,冯钰,达世禄,王忠华.β-环糊精键合固定相合成方法和色谱性能研究[J].分析测试学报, 1998, 17(5): 5–8.
[94]余品香,邓芹英,王鹏,许遵乐.β-环糊精色谱手性固定相的合成及性能表征[J].中山大学学报(自然科学版), 1998, 37(5): 53–56.
[95] Félix G, Cachau C, Thienpont A, Soulard M H. Synthesis and Chromatographic Properties of HPLC Chirai Stationary Phases Based uponβ-Cyclodextrins [J]. Chromatographia, 1996, 42(9/10): 583–588.
[96] Soukup R J, Rozhkov R V, Larock R C, Armstrong D W. The use of cyclodextrin-based LC stationary phases for the separation of chiral dihydrobenzofuran derivatives [J]. Chromatographia 2005, 61(5/6): 219–224.
[97] Armstrong D W, Stalcup A M, Hilton M L, Duncan J D, Faulkner Jr. J R, Chang S C. Derivatized cyclodextrins for normal-phase liquid chromatographic separation of enantiomers [J]. Anal. Chem., 1990,62(15): 1610–1615.
[98] Zhang Z B, Zhang W G, Luo W J, Fan J. Preparation and enantioseparation characteristics of a novel chiral stationary phase based on mono (6A-azido-6A-deoxy)-per (p-chlorophenylcarbamoylated)β-cyclodextrin [J]. J. Chromatogra. A, 2008, 1213(1-2): 162–168.
[99]柏正武,吴小聪,程志斌. 1-萘氨基甲酸酸酯β-环糊精手性固定相的合成及手性分离特性[J].分析科学学报, 2004, 20(4): 79–381.
[100] Bai Z W, Lai X H, Chen L, Ching C B, Ng S C. Arylcarbamoylated allylcarbamido-β-cyclodextrin: synthesis and immobilization on nonfunctionalized silica gel as a chiral stationary phase [J]. Tetrahedr. Lett., 2004, 45(39): 7323–7326.
[101] Zhong Q., He L, Beesley T E, Trahanovsky W S, P Sun, Wang C, Armstrong D W. Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography[J]. J. Chromatogr. A, 2006, 1115: 19–45.
[102]马海萍,李来生,陈会明,金艳红.高效液相色谱-全苯基衍生化β-环糊精短柱分离5种手性β-受体阻滞剂[J].分析化学, 2010, 38(2): 158–162.
[103]于兆文,周志强,蒋生祥,刘快之.苯甲酰化环糊精键合固定相的制备及手性拆分[J].化学试剂, 2000, 22(2): 72–74.
[104] Stalcup A M, Chang S C, Armstrong D W, Pitha J. (S)-2-Hydroxypropyl-β-cyclodextrin, a new chiral stationary phase for reversed-phase liquid chromatography [J]. J. Chromatogr A, 1990, 513: 181–194.
[105]戴荣继,郝建薇,张金专,方敏. 2, 6-二-O-苄基-β-环糊精键合硅胶固定相的合成与色谱性能[J] .北京理工大学学报, 2005, 25(1): 87–90.
[106]罗爱芹,侯爱军,戴荣继,郝建薇,刘立文.七(2, 6-二-O-丁基)-β-环糊精键合硅胶固定相的合成与评价[J].北京理工大学学报, 2005, 25(8): 745–748.
[107]黄姣,陈小明,罗和安,秦治军,曾金祥,张胜利.全戊基部分羟丙基-β-环糊精手性固定相的制备与研究[J].分析测试学报, 2004, 23(5): 93–95.
[108] Sun H Y, Bai Y, Zhao M G, Hao A Y, Xu G Y, Shen J, Li J Y, Sun T, Zhang H C. New cyclodextrin derivative 6-O-(2-hydroxybutyl)-β-cyclodextrin: preparation and its application in molecular binding and recognition [J]. Carbohydr. Res., 2009, 344(9): 1999–2004.
[109] Varga G, Tárkányi G, Németh K, Iványi R, J icsinszky L, T?ke O, Visy J, Szente L, Julianna Szemán,Miklos Simonyi. Chiral separation by a monofunctionalized cyclodextrin derivative: From selector to permethyl-β-cyclodextrin bonded stationary phase [J]. J. Pharm. Biomed. Anal., 2010, 51(1): 84–89.
[110]戴荣继,唐力,邓玉林,佟斌.生物活性环糊精衍生化蛋白质的合成[J].北京理工大学学报, 2005,25(4): 369–371.
[111]戴荣继,佟斌,唐力,邓玉林,傅若农.β-环糊精衍生化胰酶的合成及其手性分离性能研究[J].化学学报, 2006, 64(12): 1248–1252.
[112]戴荣继,佟斌,唐力,邓玉林.牛血清白蛋白-β-环糊精毛细管柱用于毛细管电色谱手性分离研究[C].郑州:第十五次全国色谱学术报告会文集, 2005: 848–849.
[113]罗爱芹,钱伟,王福明,李琰,孙立权,耿丽娜.利胆醇在新型多肽键合环糊精硅胶手性柱上分离条件的优化.北京理工大学学报, 2007, 27(7): 646–649.
[114]钱伟,梁静,李莹莹,耿丽娜,罗爱芹.新型牛血清白蛋白键合环糊精手性柱直接拆分利胆醇及其结构类似物的消旋体[C].大连:国际色谱学术报告会和展览会文集, 2007: 22–23.
[115]李莹莹,梁静,钱伟,罗爱芹.环糊精衍生牛血清白蛋白手性固定相的制备[C].苏州: 2007年全国生化与生物技术药物学术年会论文集, 2007: 114–117.
[116] Pihlainen K, Kostiainen R. Effect of the eluent on enantiomer separation of controlled drugs by liquid chromatography-ultraviolet absorbance detection electrospray ionisation tandem mass spectrometry using vancomycin and nativeβ-cyclodextrin chiral stationary phases [J]. J. Chromatogra. A, 2004, 1033(1): 91–99.
[117] Wang Y, Xiao Y, Tan T T Y, Ng S C. Click chemistry for facile immobilization of cyclodextrin derivatives onto silica as chiral stationary phases[J]. Tetrahedr. Lett. 2008. 49(35): 5190–5191.
[118] Zhang Y, Guo Z, Ye J, Xu Q, Liang X, Lei A. Preparation of novelβ-cyclodextrin chiral stationary phase based on click chemistry[J]. J. Chromatogra. A, 2008, 1191(1-2): 188–192.
[119] Wang Y, Ong T T, Li L S, Tan T T Y, Ng S C. Enantioseparation of a novel“click”chemistry derived nativeβ-cyclodextrin chiral stationary phase for high-performance liquid chromatography [J]. J. Chromatogra. A, 2009, 1216(12): 2388–2393.
[120] Guo Z, Jin Y, Liang T, Liu Y, Xu Q, Lianga X, Lei A. Synthesis, chromatographic evaluation and hydrophilic interaction/reversed-phase mixed-mode behavior of a“Clickβ-cyclodextrin”stationary phase [J]. J. Chromatogra. A, 2009, 1216(2): 257–263.
[121] L?mmerhofer M. Chiral recognition by enantioselective liquid chromatography: Mechanisms and modern chiral stationary phases [J]. J. Chromatogra. A. , 2010, 1217(6): 814–856.
[122] Ribeiro A E, Graca N S, Pais L S, Rodrigues A E. Optimization of the mobile phase composition for preparative chiral separation of flurbiprofen enantiomers [J]. Sep. Purif. Technol. 2009, 68(1): 9–12.
[123] Yao B X, Zhan F P, Yu G Y, Chen Z F, Fan W J, Zeng X P, Zeng Q L, Weng W. Temperature-induced inversion of elution order in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on an immobilized polysaccharide-based chiral stationary phase [J]. J. Chromatogr. A, 2009, 1216(28): 5429–5435.
[124] Zhan F P, Yu G Y, Yao B X, Guo X P, Liang T, Yu M G, Q L Zeng, Weng W. Solvent effect in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on a polysaccharide-based chiral stationary phase [J]. J. Chromatogr. A, 2010, 1217(26): 4278–4284.
[125] Shearer J W, Ding L, Olesik S V. Solvation parameter models for retention on perfluorinated and fluorinated low temperature glassy carbon stationary phases in reversed-phase liquid chromatography [J]. J. Chromatogra. A, 2007, 1141(1): 73–80.
[126] Nikitas P, Pappa-Louisi A. Retention models for isocratic and gradient elution in reversed-phase liquid chromatography [J]. J. Chromatogra. A, 2009, 1216(10): 1737–1755.
[127] Rosés M, Subirats X, Bosch E. Retention models for ionizable compounds in reversed-phase liquid chromatography: Effect of variation of mobile phase composition and temperature [J]. J. Chromatogra. A, 2009, 216(10): 1756–1775.
[128] Torres-LapasióJ R, Ruiz-ángel M J, García-álvarez-Coque M C. Comparative study of solvation parameter models accounting the effects of mobile phase composition in reversed-phase liquid chromatography [J]. J. Chromatogra. A, 2007, 1166(1-2): 85–96.
[129] ValkóK, Snyder L R, Glajch J L. Retention in reversed-phase liquid chromatography as a function of mobile-phase composition [J]. J. Chromatogra. A, 1993, 656(1-2): 501–520.
[130]耿信笃.计量置换理论及应用[M]北京:科学出版社, 2004:57–69.
[131]耿信鹏.液/固吸附计量置换模型及其热力学[J].纺织高校基础科学学报, 2001, 14(2): 95–101
[132] Sun R F, Yu H M, Luo H, Shen Z Y. Construction and application of a stoichiometric displacement model for retention in chiral recognition of molecular imprinting [J]. J. Chromatogra. A, 2004, 1055(1-2):1–9.
[133] Vu H, Spicer V, Gotfrid A, Krokhin O V. A model for predicting slopes S in the basic equation for the linear-solvent-strength theory of peptide separation by reversed-phase high-performance liquid chromatography [J]. J. Chromatogr. A, 2010, 1217 (4): 489–497.
[134] Fujimura K, Kitagawa M, Takayanagi H, Ando T. Optical reslution of sone mandelic derivatives on a chemically bonded cyclodextrin stationary phase[J]. J. Liq. Chromatogr., 1986, 9(2-3): 607–620.
[135] Fujimura K, Suzuki S, Hayashi K, Masuda S. Retention behavior and chiral recognition mechanism of several cyclodextrin-bonded stationary phases for dansyl amino acids[J]. Anal. Chem., 1990, 62(20): 2198–2205.
[136]于兆文,周志强,蒋生祥,陈立仁,刘快之.高效液相色谱环糊精键合固定相[J].分析测试技术与仪器, 1998, 4(4): 203–208.
[137]丁满花.β-CD及其衍生物色谱固定相的分离机理[J].零陵学院学报, 2002, 23(2): 73–76.
[138]张强,邹汉法,陈小明,汪海林,倪坚毅,张曾子,姚平径.温度对蛋白和β-环糊精手性固定相拆分对映体的影响,色谱, 2001, 19(1): 8–11.
[139] Lin C E, Lin S L, Liao W S, Liu Y C. Enantioseparation of benzoins and enantiomer migration reversal of hydrobenzoin in capillary zone electrophoresis with dual cyclodextrin systems and borate complexation [J]. J. Chromatogr. A, 2004, 1032(1-2): 227–235.
[140] Lin S L, Lin C E. Comparative studies on the enantioseparation of hydrobenzoin and structurally related compounds by capillary zone electrophoresis with sulfatedβ-cyclodextrin as the chiral selector in the presence and absence of borate complexation [J]. J. Chromatogr. A, 2004, 1032 (1-2): 213–218.
[141] KalíkováK, Jan?ckováL, Armstrong D W, Tes?rováE. Characterization of new R-naphthylethyl cyclofructan 6 chiral stationary phase and its comparison with R-naphthylethyl-cyclodextrin-based column [J]. J. Chromatogr. A, 2011, 1218(10): 1393–1398.
[142] Zhao J, Chelvi S K T, Tan D, Yong E L, Lee H K, Gong Y. Development of Vancomycin-Cappedβ-CD-Bonded Silica Particles as Chiral Stationary Phase for LC [J]. Chromatographia, 2010, 72(11/12): 1061–1066.
[143]史坚,邵芸,邹公伟.苯基异氮酸醋环糊精键合相的制备及色谱行为的研究[J].色谱, 1995, 13(6): 444–446.
[144]陈慧,吕宪禹,黄君珉,高如瑜,王琴孙.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.
[145]黄君珉,陈慧,高如瑜,王琴孙.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.
[146]周婕,杨亦文,吴平东.苯异氰酸酯基环糊精对氟西汀对映体的吸附性能[J].应用化学, 2007, 24(5): 575–579.
[147] Yong L, Gong Y H. Preparation and evaluation of calyx [4] arene-cappedβ-cyclodextrin-bonded silica particles as chiral stationary phase for high-performance liquid chromatography [J]. J. Chromatogra. A, 2008, 1203(1): 54–58.
[148]张振宾.对氯苯基氨基甲酸酯化β-环糊精手性固定相的合成及其在HPLC中的应用[D].华南师范大学, 2009: 26–88.
[149] Berchod A, Chang S C, Armstrong D W.β-cyclodextrin chiral stationary phases for liquid-chromatography-effect of the spacer alnl on chiral recognition [J]. Talanta, 1993, 40(9): 1367–1373.
[150] Stalcup A M, Chang S C, Armstrong D W, Effect of the configuration of the substituents of derivatized jkyclodextrin bonded phases on enantioselectivity in normal-phase liquid chromatography[J]. J. Chromatogr. 1991, 540: 113–128.
[151]张维平,郭鸿,高娟,耿信笃.反相液相色谱中溶剂强度规律的研究[J].色谱, 2000, 18(6): 475–479.
[2] Stephens T D, Bunde C J, Fillmore B J. Mechanism of action in thalidomide teratogenesis [J]. Biochem. Pharmacol., 2000, 59(12): 1489–1499.
[3]张玮,尚平,姚军.手性药物与手性分离技术[J].河北化工, 2004, 27(5): 12–14.
[4]宫丽,卞俊.手性药物的药理学立体选择性[J].国外医学·药学分册, 2007, 34(2):123–126.
[5] Patel R N. Biocatalytic Synthesis of Chiral Pharmaceutical Intermediates [J]. Food Technol. Biotechnol, 2004, 42(4): 305–325.
[6] Liu M, Li L S, Da S L, Feng Y Q. High performance liquid chromatography with cyclodextrin and calixarene macrocycle bonded silica stationary phases for separation of steroids [J]. Talanta, 2005, 66(2): 479–486.
[7] Lin C H, Chen C Y, Chang S W, Wu J C, Lin C E. Use ofβ-cyclodextrin bonded phase with s-triazine moiety in the spacer for separation of aromatic carboxylic acid isomers by high-performance liquid chromatography [J]. Anal. Chim. Acta, 2006, 576(1): 84–90.
[8] Campos-Candel A, Llobat-Estellés M, Mauri-Aucejo A. Comparative evaluation of liquid chromatography versus gas chromatography using aβ-cyclodextrin stationary phase for the determination of BTEX in occupational environments [J]. Talanta, 2009, 78 () 1286–1292.
[9] Schleuder M, Durrbeck A, Jira T. The Influence of Cyclodextrin on the Stability of Cephalotin and Aztreomam in Aqueous Slution [J]. Pharmazie, 1998, 53 (6): 381–386.
[10]杨欣欣,陈国文,赵士贵,王峰,王旭波.环糊精及其衍生物在气相色谱中的应用进展[J].山东化工, 2007, 36(4): 11–13.
[11]李晓霞,王佳.环糊精类固定相在气相色谱中的应用[J].延安大学学报(自然科学版), 2004, 23(2): 64–69.
[12]尹明明.环糊精类气谱手性固定相的合成及其手性分离性能的研究[D].北京:中国农业大学, 2006: 4–6.
[13]李清华.气相色谱法测定羟丙基-β-环糊精平均取代度[J].应用化工, 2009, 28(1): 139–141.
[14]陶旦妮,史雪岩,顾峻岭,傅若农.环糊精衍生物固定相毛细管气相色谱法分离甲酚位置异构体[J].分析化学, 2001, 29(10): 1150–1153.
[15] Krup?ík J, MájekováM, Májek P, Hrouzek J, Benicka E, Onuska F, Sandra P, Zeeuw J. On the interconversion energy barriers obtained for atropisomers of some polychlorinated biphenyls by AM1 semiempirical quantum chemistry method and gas chromatography on a modified cyclodextrin stationary phase [J]. Anal. chem., 1995, 352(7-8): 696–698.
[16] Abe I, Nishiyama T, Nakahara T, Frank H. Gas chromatographic enantiomer separation of pharmaceuticals on capillary columns coated with novel chiral polysiloxanes [J]. J. Chromatogr. A, 1995, 694(1): 237–243.
[17] Bicchi C, D’Amato A, Rubiolo P. cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oilmaroma and flavours fields [J]. J. Chromatogr. A, 1999, 843 (1-2)99–121.
[18] Quattrini F, Biressi G, Juza M, Mazzotti M, Fuganti C, Morbidelli M. Enantiomer separation of a-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases [J]. J. Chromatogra. A, 1999, 865(1-2): 201–210.
[19] Schurig V. Separation of enantiomers by gas chromatography [J]. J. Chromatogra. A, 2001, 906(1-2): 275–299.
[20] K?nigW A, Lutz S, Wenz G, Bey E. Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part II: Heptakis (3-O-acetyl-2, 6-di-O-pentyl)-?-cyclodextrin [J]. J. High. Resolut. Chromatogr., 1988, 11(7): 506–509.
[21] Shi X, Guo H, Wang M. Enantioseparation of chiral epoxides using four new cyclodextrin derivatives as chiral stationary phases of capillary gas chromatography [J]. Anal. Chim. Acta, 2005, 553(1-2) 43–49.
[22] Shi X, Liang P, Gao X. The capillary gas chromatographic properties of fourβ-cyclodextrin derivatives with allyl groups or propyl groups on 3-position or 6-position ofβ-cyclodextrin [J]. Anal. Chim. Acta, 2005, 548(1-2): 86–94.
[23] Mallmann A S, Ethur E M, Silva U F, Dalcol I I, Morel A F. Synthesis and Chromatographic Evaluation of the New Phase Heptakis (3-O-pentafluoropropionyl- 2,6-di-O-pentyl)-β-cyclodextrin [J]. J. Braz. Chem. Soc., 2010, 21(10): 2005–2011.
[24] McGachy N T, Grinberg N, Variankaval N. Thermodynamic study of N-trifluoroacetyl-O-alkylnipecotic acid ester enantiomers on diluted permethylated- cyclodextrin stationary phase [J]. J. Chromatogra. A, 2005, 1064(2): 193–204.
[25]周美杨,凌云,申刚义,杨新玲.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能[J].高等学校化学学报, 2008, 29(3): 493–497.
[26]申刚义,崔箭,杨新玲,周美杨,凌云.一种吡啶杂环β-环糊精固定相的制备及其气相色谱分离性能[J].理化检验-化学分册, 2009, 45(2):222–224.
[27]朱小波,陈福良,尹明明.全烷基化β-环糊精混合固定相上一些取代苯类手性化合物的气相色谱分离研究[J]. 2009, 28(4):409-413.
[28] Huang K, Armstrong D W, Forro E, Fulop F, Peter A. Separation of Enantiomers and Control of Elution Order ofβ-Lactams by GC Using Cyclodextrin-Based Chiral StationaryPhases [J]. Chromatographia, 2009, 69(3-4): 331–337.
[29] Akapo S, McCrea C, Gupta J, Roach M, Skinner W. Chiral HPLC analysis of formoterol stereoisomers and thermodynamic study of their interconversion in aqueous pharmaceutical formulations [J]. J. Pharmaceutical and Biomedical Anal., 2009, 49(3): 632–637.
[30] Al-Majed A A. A direct HPLC method for the resolution and quantitation of the R-(?)- and S-(+)-enantiomers of vigabatrin (γ-vinyl-GABA) in pharmaceutical dosage forms using teicoplanin aglycone chiral stationary phase[J] . J. Pharm. Biomed. Anal., 2009, 50(1): 96–99.
[31] Easton C, Lincoln S. Chiral discrimination by modified cyclodextrins [J]. Chem. Soc. Rev., 1996, 25(1): 163–170.
[32] Armstrong D W, DeMond W, Cyclodextrin bonded phases for the liquid chromatographic separation of optical, geometrical, and structural isomers [J]. J. Chromatogr. Sci., 1984, 22(9): 411–415.
[33]阮源萍,张雪曼,陈安齐. 2,6-二-O-烷基-β-环糊精涂渍手性固定相分离联萘酚类对映异构体[J].厦门大学学报(自然科学版), 2004, 43(3): 8–92.
[34]曾苏.高效液相色谱手性流动相添加剂法分离药物对映体[J].色谱, 1995, 13(1): 21–25.
[35] Toyohide T, Homare A, Daido S. Enantiomeric resolution of dansyl amino acids by micro high-performance liquid chromatography withβ-cyclodextrin inclusion complexes [J]. J. Chromatogr., 1986, 357: 409–415.
[36]姚彤炜,曾苏,丁海青.环糊精类手性流动相添加剂及其在药物分析中的应用[J].色谱, 1996,14(2): 106–110.
[37]李桦,胡先明,谢颖峰.高效液相色谱手性流动相添加剂分离肾上腺素类对映体[J].色谱, 1998, 16(5): 424–426.
[38] Schmid M G, H?rringer B, Gübitz G. Chiral Resolution of RR,SS-Hydrobenzoin by Liquid Chromatography Using Borate-Cyclodextrin Complexation [J]. J. High Resol. Chromatogr.1998, 21(7): 414–416.
[39]宁凤容,黄可龙,焦飞鹏. HP-β-CD手性流动相HPLC法拆分萘普生对映体的色谱保留机制和拆分机理研究[J].化学通报, 2006, (6): 425–429.
[40]周采菊,刘瑛. HPLC手性流动相添加剂法拆分马来酸氨氯地平[J].中国现代应用药学, 2009, 26(9): 757–759.
[41] Ma S, Shen S, Haddad N, Tang W, Wang J, Lee H, Yee N, Senanayake C, Grinberg N. Chromatographic and spectroscopic studies on the chiral recognition of sulfatedβ-cyclodextrin as chiral mobile phase additive: Enantiomeric separation of a chiral amine [J]. J.Chromatogra. A, 2009, 216(8): 1232–1240.
[42] Weng W, Wang Q H, Yao B X, Zeng Q L. Enantioseparation of amino acid derivatives on an immobilized network polymer derived from L-tartaric acid [J]. J. Chromatogr. A, 2004, 1042(1-2): 81–87 [[43]翁文,林敏,钟艺聪. L-酒石酸型固定相对映分离氨基酸衍生物[J].分析化学, 2004, 32(2): 213–216.
[44]唐琴.高效液相色谱手性固定相法拆分药物对映体研究[D].四川:四川大学. 2004: 15–17.
[45] Weng W, Zeng Q L, Wang Q H. Influence of mobile phase composition on the apparent thermodynamic characteristics in the high performance liquid chromatographic enantioseparation on a tartaric acid derivatized network polymer [J]. Chromatographia, 2005, 61(11-12): 561–566.
[46]翁文,姚碧霞,陈秀琴,陈友遵,林文士,曾庆乐.液相色谱手性拆分机理的热力学方法研究[J]化学进展, 2006, 18(7/8): 1056–1064.
[47] Weng W, Zeng Q L, Yao B X. Enantioseparation of Amino Acid Derivatives with a Cellulose-Based Stationary Phase [J]. Chromatographia, 2006, 64(7-8): 463–467.
[48]翁文,林文士,姚碧霞.纤维素型手性固定相拆分亚砜系列化合物[J].分析化学, 2006, 34(6): 805–808.
[49]翁文,范文静,朱钦.联萘系列化合物在甘氨酸型手性固定相上的拆分[J].分析测试学报, 2008, 27(7):721–724.
[50] Weng W, Zhan F P, Fu J, Li T, Chen X,.Huang X. Enantioseparation of binaphthol and its derivatives on cellulose tris (3, 5-dimethylphenyl carbamate) [J]. Chromatographia, 2008, 67(1-2): 119–123.
[51]陈立仁.液相色谱手性分离[M].北京:科学出版社, 2006: 35-80.
[52] Malik A, Jinno K. Retention Behaviour of Aromatic Compounds in Liquid Chromatography and Supercritical Fluid Chromatography with Coarse-Particles of Bondedβ-Cyclodextrin Stationary Phase[J]. Chromatographia, 1991, 31(11/12): 561–568.
[53] Shen Y, Chen Z, Owen N L, Li W, Bradshaw J S, Lee M L. Cyclodextrin polymer encapsulated particles for supercritical fluid chromatography [J]. J. Microcolumn Sep., 1996, 8(4): 249–257.
[54] Wang R Q, Ong T T, Ng S C. Synthesis of cationicβ-cyclodextrin derivatives and their applications as chiral stationary phases for high-performance liquid chromatography and supercritical fluid chromatography [J]. J. Chromatogra. A, 2008, 1203(2): 185–192.
[55]申丽红.超临界介质中卤代离子液体的合成及其在β-环糊精改性中的应用[D].西安:陕西师范大学, 2008: 17–19.
[56] Aumatell A, Guttman A. Ultra-fast chiral separation of basic drugs by capillary electrophoresis [J]. J. Chromatogr. A, 1995, 717(1-2): 22–234.
[57] Stalcup A M, Gahm K H. A sulfated cyclodextrin chiral stationary phase for high-performance liquid chromatography[J]. Anal Chem, 1996, 68(8): 1360-1368
[58] Gubitz G, Schmid M G. Chiral separation principles in capillary electrophoresis [J]. J. Chromatogr. A, 1997, 792(1-2): 179–225.
[59] Schmid M G, Wirnsberger K, Jira T, Bunke A, Gubitz G. Capillary Electrophoretic Chiral Resolution of Vicinal Diols by Complexation With Borate and Cyclodextrin: Comparative Studies on Different Cyclodextrin Derivatives [J]. Chirality, 1997, 9(2): 153–156.
[60] Stádberg O, Hedeland M, Pettersson C, Westerlund D. The Effect of Conductivity Tuning in Chiral Separations by CE: Using Hydroxypropyl-13- Cyclodextrin in Combination with Tetraalkylammonium lons [J]. Chromatographia, 1998, 48(5-6): 415–421.
[61] Zhou A, Lv X, Xie Y, Yan C, Gao R. Chromatographic evaluation of perphenylcarbamoylatedβ-cyclodextrin bonded stationary phase for micro-high performance liquid chromatography and pressurized capillary electrochromatography [J]. Anal. Chim. Acta, 2005, 547(2): 158–164.
[62]马剑茵.手性药物的色谱分离方法[J].中国医药工业杂志, 2002, 33(4): 199–202.
[63]朱晓峰,林炳承.毛细管区带电泳法拆分手性药物萘普生和氟联苯丙酸[J].色谱, 2000, 18(1): 70–72.
[64]史雪岩,梁沛,宋敦伦,高希武.聚合-β-环糊精作手性添加剂的毛细管电泳法分离4种光学活性农药中间体[J].分析化学, 2004, 32(11): 1421–1425.
[65] Wang J, Yuan Q, Evans D G, Yang L, Zheng G, Sun W. Enantioselective separation of phenylglycidates by capillary electrophoresis employing sulfatedβ-cyclodextrin as chiral selector [J]. J. Chromatogra. B, 2007, 850(1-2): 560–563.
[66]夏陈,陈志涛,夏之宁.基于非手性离子液体的毛细管电泳法拆分3种手性药物[J].色谱, 2008, 26(6): 677–681.
[67]郑志侠,汪家权,程红,肖莆.基于环糊精手性选择剂的几种手性药物对映体的毛细管电泳拆分[J].化学研究, 2010, 21(1): 76–79.
[68] Zhu H, Wu E, Chen, J Jang Y S, Kang W, Choi J K, Lee W, Kang J S. Reverse migration order of sibutramine enantiomers as a function of cyclodextrin concentration in capillary electrophoresis [J]. J. Pharm. Biomed. Anal., 2011, 54(5): 1007–1012.
[69] Zaidi S A, Lee S M, Cheong W J. Open tubular capillary columns with basic templates made by the generalized preparation protocol in capillary electrochromatography chiral separation and template structural effects on chiral separation capability [J]. J. Chromatogra. A, 2011, 1218 (9): 1291–1299.
[70] Szejtli J. Cyclodextrin and their inclusion complexes [M]. Budapest: Akademiai Kiado, 1982:277–289.
[71] Breslow R, Zhang X, Xu R, Maletic M, Merger R. Selective catalytic oxidation of substrates That Bind to Metalloporphyrin Enzyme Mimics Carrying Two or Four Cyclodextrin Groups and Related Metallosalens [J]. J. Am. Chem. Soc., 1996, 118(46): 11678–11679.
[72]张雪飞.环糊精的研究进展及其应用[J].内蒙古民族大学学报, 2010, 16(5):31–32.
[73]廖才智.β-环糊精的应用研究进展[J].化工科技, 2010, 18(5): 69–72.
[74]凌云,傅若农.环糊精衍生物固定相在色谱分离光活性化合物中的应用进展[J].化学试剂, 1996, 18(1): 19–24.
[75]张纪贵,郝爱友.β-环糊精固定相在色谱中的应用及发展趋势[J].化学研究与应用, 2003, 15(3): 303–306.
[76] Thuaud N, Sébille B, Deratani A, Lelièvre G. Retention behavior and chiral recognition ofβ-cyclodextrin-derivative polymer adsorbed on silica for warfarin, structurally related compounds and Dns-amino acids [J]. J. Chromatogr., 1991, 555(1-2): 53–64.
[77] Thuaud N, Sébille B, Deratani A, P?pping B, Pellet C. Enantiomer separations with chromatographic supports based onβ-cyclodextrin polymers immobilized on porous silica: role of the polymer structure in separating ability [J]. Chromatographia, 1993, 36(23): 373–380.
[78] Crini G, Morcellet M, Torri G. HPLC of structural isomers with cyclodextrin-poly (vinylamine)-coated silica columns, Part I: Synthesis and characterization of cyclodextrin-bonded stationary phases by NMR solid state [J]. J. Chromatogr. Sci., 1996, 34(11): 477–484.
[79] Crini G, Morcellet M, Torri G. HPLC of structural isomers using cyclodextrin-poly (vinylamine)-coated silica columns, Part II: Retention behavior and separation [J]. J. Chromatogr. Sci., 1996, 34(11): 485–494.
[80] Thuaud N, G Lelièvre, Deratani A, Sébille B. Preparation of chiral stationary phases by graftingβ-CD derivatives on polyvinylimidazole coated silica [J]. Eur. Polym. J., 1997, 33(7): 1015–1020.
[81] Ong T T, Wang R Q, Muderawan I W, Ng S C. Synthesis and application of mono-6-(3-methylimidazolium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride as chiral stationary phases for high-performance liquid chromatography and supercritical fluid chromatography[J]. J. Chromatogra. A, 2008, 1182 (1): 136–140.
[82] Yin M M, Zhu X B, Liu Y L, Zhong J C, Chen F L. Synthesis of heptakis(2,3,6-tri-O-methoxymethyl)-β-cyclodextrin and its application in gas chromatography [J]. Chinese J. Chromatogra., 2011, 29(01): 91–94.
[83]都振华,王莉晶. N-叔丁氧羰基-L-丙氨酸衍生化环糊精键合硅胶固定相的合成与性能研究[J].工程技术, 2009, (22): 31–32.
[84] Lai X H, Ng S C. Convenient synthesis of mono (6A-N-allylamino-6A-deoxy)-permethylatedβ-cyclodextrin: a promising chiral selector for an HPLC chiral stationary phase [J]. Tetrahedr. Lett. 2004, 45(23): 4469–4472.
[85]罗爱芹,刘立文,戴荣继,郝建薇,张金专,方敏. 2, 6-二-O-苄基-β-环糊精键合硅胶固定相的合成与色谱性能[J].北京理工大学学报, 2005, 25(1): 87–90.
[86] Franco E, Senso A, Olivems L, Minguillon C. Covalently bonded polysaccharide derivatives as chiral stationaryphases in high-performance liquid chromatography [J]. J. Chromatogr. 2001, 906(1-2): 155–170.
[87] Muderawan I W, Ong T T, Ng S C. Urea bonded cyclodextrin derivatives onto silica for chiral HPLC[J]. J. Sep. Sci., 2006, 29(12): 1849–1871.
[88]冯钰锜,达世禄.甘氨酸衍生化β-环糊精键合硅胶液相色谱固定相的合成与评价[J].色谱, 2000, 18(3): 224–228.
[89]杨少宁,罗爱芹,侯爱军. 3, 5-二硝基苯甲酰化β-环糊精键合硅胶手性固定相的合成及高效液相色谱中的手性分离研究[J].分析科学学报, 2008, 24(5): 615–617.
[90] Thamarai C S K, Yong E L, Gong Y. Preparation and evaluation of calix[4]arene-cappedβ-cyclodextrin-bonded silica particles as chiral stationary phase for high-performance liquid chromatography [J]. J. Chromatogra. A, 2008, 1203(1) 54–58.
[91]陈立仁.液相色谱手性分离[M].北京:科学出版社, 2006: 107–108.
[92]黄天宝,吴邦桂,龙远德,旷昌渝,周竞先.β-CD键合固定相的制备和评价[J].分析化学, 1991, 19(11): 1257–1260.
[93]龚银汉,董亚琼,冯钰,达世禄,王忠华.β-环糊精键合固定相合成方法和色谱性能研究[J].分析测试学报, 1998, 17(5): 5–8.
[94]余品香,邓芹英,王鹏,许遵乐.β-环糊精色谱手性固定相的合成及性能表征[J].中山大学学报(自然科学版), 1998, 37(5): 53–56.
[95] Félix G, Cachau C, Thienpont A, Soulard M H. Synthesis and Chromatographic Properties of HPLC Chirai Stationary Phases Based uponβ-Cyclodextrins [J]. Chromatographia, 1996, 42(9/10): 583–588.
[96] Soukup R J, Rozhkov R V, Larock R C, Armstrong D W. The use of cyclodextrin-based LC stationary phases for the separation of chiral dihydrobenzofuran derivatives [J]. Chromatographia 2005, 61(5/6): 219–224.
[97] Armstrong D W, Stalcup A M, Hilton M L, Duncan J D, Faulkner Jr. J R, Chang S C. Derivatized cyclodextrins for normal-phase liquid chromatographic separation of enantiomers [J]. Anal. Chem., 1990,62(15): 1610–1615.
[98] Zhang Z B, Zhang W G, Luo W J, Fan J. Preparation and enantioseparation characteristics of a novel chiral stationary phase based on mono (6A-azido-6A-deoxy)-per (p-chlorophenylcarbamoylated)β-cyclodextrin [J]. J. Chromatogra. A, 2008, 1213(1-2): 162–168.
[99]柏正武,吴小聪,程志斌. 1-萘氨基甲酸酸酯β-环糊精手性固定相的合成及手性分离特性[J].分析科学学报, 2004, 20(4): 79–381.
[100] Bai Z W, Lai X H, Chen L, Ching C B, Ng S C. Arylcarbamoylated allylcarbamido-β-cyclodextrin: synthesis and immobilization on nonfunctionalized silica gel as a chiral stationary phase [J]. Tetrahedr. Lett., 2004, 45(39): 7323–7326.
[101] Zhong Q., He L, Beesley T E, Trahanovsky W S, P Sun, Wang C, Armstrong D W. Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography[J]. J. Chromatogr. A, 2006, 1115: 19–45.
[102]马海萍,李来生,陈会明,金艳红.高效液相色谱-全苯基衍生化β-环糊精短柱分离5种手性β-受体阻滞剂[J].分析化学, 2010, 38(2): 158–162.
[103]于兆文,周志强,蒋生祥,刘快之.苯甲酰化环糊精键合固定相的制备及手性拆分[J].化学试剂, 2000, 22(2): 72–74.
[104] Stalcup A M, Chang S C, Armstrong D W, Pitha J. (S)-2-Hydroxypropyl-β-cyclodextrin, a new chiral stationary phase for reversed-phase liquid chromatography [J]. J. Chromatogr A, 1990, 513: 181–194.
[105]戴荣继,郝建薇,张金专,方敏. 2, 6-二-O-苄基-β-环糊精键合硅胶固定相的合成与色谱性能[J] .北京理工大学学报, 2005, 25(1): 87–90.
[106]罗爱芹,侯爱军,戴荣继,郝建薇,刘立文.七(2, 6-二-O-丁基)-β-环糊精键合硅胶固定相的合成与评价[J].北京理工大学学报, 2005, 25(8): 745–748.
[107]黄姣,陈小明,罗和安,秦治军,曾金祥,张胜利.全戊基部分羟丙基-β-环糊精手性固定相的制备与研究[J].分析测试学报, 2004, 23(5): 93–95.
[108] Sun H Y, Bai Y, Zhao M G, Hao A Y, Xu G Y, Shen J, Li J Y, Sun T, Zhang H C. New cyclodextrin derivative 6-O-(2-hydroxybutyl)-β-cyclodextrin: preparation and its application in molecular binding and recognition [J]. Carbohydr. Res., 2009, 344(9): 1999–2004.
[109] Varga G, Tárkányi G, Németh K, Iványi R, J icsinszky L, T?ke O, Visy J, Szente L, Julianna Szemán,Miklos Simonyi. Chiral separation by a monofunctionalized cyclodextrin derivative: From selector to permethyl-β-cyclodextrin bonded stationary phase [J]. J. Pharm. Biomed. Anal., 2010, 51(1): 84–89.
[110]戴荣继,唐力,邓玉林,佟斌.生物活性环糊精衍生化蛋白质的合成[J].北京理工大学学报, 2005,25(4): 369–371.
[111]戴荣继,佟斌,唐力,邓玉林,傅若农.β-环糊精衍生化胰酶的合成及其手性分离性能研究[J].化学学报, 2006, 64(12): 1248–1252.
[112]戴荣继,佟斌,唐力,邓玉林.牛血清白蛋白-β-环糊精毛细管柱用于毛细管电色谱手性分离研究[C].郑州:第十五次全国色谱学术报告会文集, 2005: 848–849.
[113]罗爱芹,钱伟,王福明,李琰,孙立权,耿丽娜.利胆醇在新型多肽键合环糊精硅胶手性柱上分离条件的优化.北京理工大学学报, 2007, 27(7): 646–649.
[114]钱伟,梁静,李莹莹,耿丽娜,罗爱芹.新型牛血清白蛋白键合环糊精手性柱直接拆分利胆醇及其结构类似物的消旋体[C].大连:国际色谱学术报告会和展览会文集, 2007: 22–23.
[115]李莹莹,梁静,钱伟,罗爱芹.环糊精衍生牛血清白蛋白手性固定相的制备[C].苏州: 2007年全国生化与生物技术药物学术年会论文集, 2007: 114–117.
[116] Pihlainen K, Kostiainen R. Effect of the eluent on enantiomer separation of controlled drugs by liquid chromatography-ultraviolet absorbance detection electrospray ionisation tandem mass spectrometry using vancomycin and nativeβ-cyclodextrin chiral stationary phases [J]. J. Chromatogra. A, 2004, 1033(1): 91–99.
[117] Wang Y, Xiao Y, Tan T T Y, Ng S C. Click chemistry for facile immobilization of cyclodextrin derivatives onto silica as chiral stationary phases[J]. Tetrahedr. Lett. 2008. 49(35): 5190–5191.
[118] Zhang Y, Guo Z, Ye J, Xu Q, Liang X, Lei A. Preparation of novelβ-cyclodextrin chiral stationary phase based on click chemistry[J]. J. Chromatogra. A, 2008, 1191(1-2): 188–192.
[119] Wang Y, Ong T T, Li L S, Tan T T Y, Ng S C. Enantioseparation of a novel“click”chemistry derived nativeβ-cyclodextrin chiral stationary phase for high-performance liquid chromatography [J]. J. Chromatogra. A, 2009, 1216(12): 2388–2393.
[120] Guo Z, Jin Y, Liang T, Liu Y, Xu Q, Lianga X, Lei A. Synthesis, chromatographic evaluation and hydrophilic interaction/reversed-phase mixed-mode behavior of a“Clickβ-cyclodextrin”stationary phase [J]. J. Chromatogra. A, 2009, 1216(2): 257–263.
[121] L?mmerhofer M. Chiral recognition by enantioselective liquid chromatography: Mechanisms and modern chiral stationary phases [J]. J. Chromatogra. A. , 2010, 1217(6): 814–856.
[122] Ribeiro A E, Graca N S, Pais L S, Rodrigues A E. Optimization of the mobile phase composition for preparative chiral separation of flurbiprofen enantiomers [J]. Sep. Purif. Technol. 2009, 68(1): 9–12.
[123] Yao B X, Zhan F P, Yu G Y, Chen Z F, Fan W J, Zeng X P, Zeng Q L, Weng W. Temperature-induced inversion of elution order in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on an immobilized polysaccharide-based chiral stationary phase [J]. J. Chromatogr. A, 2009, 1216(28): 5429–5435.
[124] Zhan F P, Yu G Y, Yao B X, Guo X P, Liang T, Yu M G, Q L Zeng, Weng W. Solvent effect in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on a polysaccharide-based chiral stationary phase [J]. J. Chromatogr. A, 2010, 1217(26): 4278–4284.
[125] Shearer J W, Ding L, Olesik S V. Solvation parameter models for retention on perfluorinated and fluorinated low temperature glassy carbon stationary phases in reversed-phase liquid chromatography [J]. J. Chromatogra. A, 2007, 1141(1): 73–80.
[126] Nikitas P, Pappa-Louisi A. Retention models for isocratic and gradient elution in reversed-phase liquid chromatography [J]. J. Chromatogra. A, 2009, 1216(10): 1737–1755.
[127] Rosés M, Subirats X, Bosch E. Retention models for ionizable compounds in reversed-phase liquid chromatography: Effect of variation of mobile phase composition and temperature [J]. J. Chromatogra. A, 2009, 216(10): 1756–1775.
[128] Torres-LapasióJ R, Ruiz-ángel M J, García-álvarez-Coque M C. Comparative study of solvation parameter models accounting the effects of mobile phase composition in reversed-phase liquid chromatography [J]. J. Chromatogra. A, 2007, 1166(1-2): 85–96.
[129] ValkóK, Snyder L R, Glajch J L. Retention in reversed-phase liquid chromatography as a function of mobile-phase composition [J]. J. Chromatogra. A, 1993, 656(1-2): 501–520.
[130]耿信笃.计量置换理论及应用[M]北京:科学出版社, 2004:57–69.
[131]耿信鹏.液/固吸附计量置换模型及其热力学[J].纺织高校基础科学学报, 2001, 14(2): 95–101
[132] Sun R F, Yu H M, Luo H, Shen Z Y. Construction and application of a stoichiometric displacement model for retention in chiral recognition of molecular imprinting [J]. J. Chromatogra. A, 2004, 1055(1-2):1–9.
[133] Vu H, Spicer V, Gotfrid A, Krokhin O V. A model for predicting slopes S in the basic equation for the linear-solvent-strength theory of peptide separation by reversed-phase high-performance liquid chromatography [J]. J. Chromatogr. A, 2010, 1217 (4): 489–497.
[134] Fujimura K, Kitagawa M, Takayanagi H, Ando T. Optical reslution of sone mandelic derivatives on a chemically bonded cyclodextrin stationary phase[J]. J. Liq. Chromatogr., 1986, 9(2-3): 607–620.
[135] Fujimura K, Suzuki S, Hayashi K, Masuda S. Retention behavior and chiral recognition mechanism of several cyclodextrin-bonded stationary phases for dansyl amino acids[J]. Anal. Chem., 1990, 62(20): 2198–2205.
[136]于兆文,周志强,蒋生祥,陈立仁,刘快之.高效液相色谱环糊精键合固定相[J].分析测试技术与仪器, 1998, 4(4): 203–208.
[137]丁满花.β-CD及其衍生物色谱固定相的分离机理[J].零陵学院学报, 2002, 23(2): 73–76.
[138]张强,邹汉法,陈小明,汪海林,倪坚毅,张曾子,姚平径.温度对蛋白和β-环糊精手性固定相拆分对映体的影响,色谱, 2001, 19(1): 8–11.
[139] Lin C E, Lin S L, Liao W S, Liu Y C. Enantioseparation of benzoins and enantiomer migration reversal of hydrobenzoin in capillary zone electrophoresis with dual cyclodextrin systems and borate complexation [J]. J. Chromatogr. A, 2004, 1032(1-2): 227–235.
[140] Lin S L, Lin C E. Comparative studies on the enantioseparation of hydrobenzoin and structurally related compounds by capillary zone electrophoresis with sulfatedβ-cyclodextrin as the chiral selector in the presence and absence of borate complexation [J]. J. Chromatogr. A, 2004, 1032 (1-2): 213–218.
[141] KalíkováK, Jan?ckováL, Armstrong D W, Tes?rováE. Characterization of new R-naphthylethyl cyclofructan 6 chiral stationary phase and its comparison with R-naphthylethyl-cyclodextrin-based column [J]. J. Chromatogr. A, 2011, 1218(10): 1393–1398.
[142] Zhao J, Chelvi S K T, Tan D, Yong E L, Lee H K, Gong Y. Development of Vancomycin-Cappedβ-CD-Bonded Silica Particles as Chiral Stationary Phase for LC [J]. Chromatographia, 2010, 72(11/12): 1061–1066.
[143]史坚,邵芸,邹公伟.苯基异氮酸醋环糊精键合相的制备及色谱行为的研究[J].色谱, 1995, 13(6): 444–446.
[144]陈慧,吕宪禹,黄君珉,高如瑜,王琴孙.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.
[145]黄君珉,陈慧,高如瑜,王琴孙.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.
[146]周婕,杨亦文,吴平东.苯异氰酸酯基环糊精对氟西汀对映体的吸附性能[J].应用化学, 2007, 24(5): 575–579.
[147] Yong L, Gong Y H. Preparation and evaluation of calyx [4] arene-cappedβ-cyclodextrin-bonded silica particles as chiral stationary phase for high-performance liquid chromatography [J]. J. Chromatogra. A, 2008, 1203(1): 54–58.
[148]张振宾.对氯苯基氨基甲酸酯化β-环糊精手性固定相的合成及其在HPLC中的应用[D].华南师范大学, 2009: 26–88.
[149] Berchod A, Chang S C, Armstrong D W.β-cyclodextrin chiral stationary phases for liquid-chromatography-effect of the spacer alnl on chiral recognition [J]. Talanta, 1993, 40(9): 1367–1373.
[150] Stalcup A M, Chang S C, Armstrong D W, Effect of the configuration of the substituents of derivatized jkyclodextrin bonded phases on enantioselectivity in normal-phase liquid chromatography[J]. J. Chromatogr. 1991, 540: 113–128.
[151]张维平,郭鸿,高娟,耿信笃.反相液相色谱中溶剂强度规律的研究[J].色谱, 2000, 18(6): 475–479.