2-氨基蒽醌柱前衍生化糖类物质的分析
|
摘要
高效液相色谱(HPLC)已经成为糖类物质分离分析的重要工具。由于糖类物质没有光学活性,因此需要通过衍生化的方法使之带上紫外或荧光集团才能实现在HPLC上分离检测。目前已经开发了很多种类的衍生化试剂,但是大多都存在一些不足如衍生化流程繁琐、不同的反应样品需要摸索不同的反应条件、产生副产物、质谱检测灵敏度不高等,所以寻找新的性能优良的衍生化试剂很有意义。本文首次选用了2-氨基蒽醌作为糖的标记试剂,建立了糖柱前衍生化的高效液相色谱(HPLC)以及电喷雾质谱(ESI-MS)分析方法,取得了较好的效果,表明该方法在糖类物质的分析方面有潜在的应用价值。本研究主要得到了以下的结果和结论。
1.实验中探讨了各种衍生化条件对产率的影响,并对这些条件加以优化。优化后的衍生化方法条件温和,70℃反应60min即可完成,反应完全。
2.将五种单糖标准进行柱前衍生化,考察了此衍生化方法的稳定性、线性关系和最低检测限(LOD)、回收率等指标,建立了较为理想的单糖分析模式,成功地测定了白芨BSPI-A组分的单糖组成。
3.将2-氨基蒽醌用于寡糖混合物的分离,建立了一套寡糖混合物柱前衍生化的HPLC-ESI-MS组分分析方法。表明该方法在食品体系寡糖混合物分离分析方面有的应用前景。
High Performance Liquid Chromatography(HPLC) had became an important tool in the analysis of carbohydrates due to its efficiency and high-speed. because of the sugers had no optical activity,they can not be well detected on the HPLC until we supplied a ultraviolet or fluorescence group for them through derivatization reaction.A great many of derivatization reagent had been introduced,but they had many shortages such as its complex derivatization procedures,its different reaction conditions for different samples,its by-products,its less sensitivity on MS. So it was worth to try new functional reagents which can meet the need of analyzing the sugers.In this paper,we established a new HPLC and ESI-MS analysis method of carbohydrates by 2-Aminoanthraquinone pre-column derivatization based on reductive amination,and the results were nice. The developed dervatizationi method had potential application outlook for the analysis of mixed oligosaccharides.
1. Derivatization conditions which affected the reaction productivity were discussed and optimized. The reaction was very mild and can be completed under 70℃、60min.
2. The five monosaccharide standers were pe-column derived using 2-Aminoanthraquinone. we studied the reaction indexs such as stability、linear relation and lowest detectable limit and so on.Then established desired analysis model for monosaccharides. We successfully analyzed the nonosaccharides composition of BSPI-A from Bletilla striata.
3. The means to separate and analyze mixed oligosaccharides using HPL、ESI-MS、LC-ESI-MS was successfully established, which was based on a new reagent 2-Aminoanthraquinone. This method had potential application prospect for the analysis of complicated oligosaccharides of food system.
1.实验中探讨了各种衍生化条件对产率的影响,并对这些条件加以优化。优化后的衍生化方法条件温和,70℃反应60min即可完成,反应完全。
2.将五种单糖标准进行柱前衍生化,考察了此衍生化方法的稳定性、线性关系和最低检测限(LOD)、回收率等指标,建立了较为理想的单糖分析模式,成功地测定了白芨BSPI-A组分的单糖组成。
3.将2-氨基蒽醌用于寡糖混合物的分离,建立了一套寡糖混合物柱前衍生化的HPLC-ESI-MS组分分析方法。表明该方法在食品体系寡糖混合物分离分析方面有的应用前景。
High Performance Liquid Chromatography(HPLC) had became an important tool in the analysis of carbohydrates due to its efficiency and high-speed. because of the sugers had no optical activity,they can not be well detected on the HPLC until we supplied a ultraviolet or fluorescence group for them through derivatization reaction.A great many of derivatization reagent had been introduced,but they had many shortages such as its complex derivatization procedures,its different reaction conditions for different samples,its by-products,its less sensitivity on MS. So it was worth to try new functional reagents which can meet the need of analyzing the sugers.In this paper,we established a new HPLC and ESI-MS analysis method of carbohydrates by 2-Aminoanthraquinone pre-column derivatization based on reductive amination,and the results were nice. The developed dervatizationi method had potential application outlook for the analysis of mixed oligosaccharides.
1. Derivatization conditions which affected the reaction productivity were discussed and optimized. The reaction was very mild and can be completed under 70℃、60min.
2. The five monosaccharide standers were pe-column derived using 2-Aminoanthraquinone. we studied the reaction indexs such as stability、linear relation and lowest detectable limit and so on.Then established desired analysis model for monosaccharides. We successfully analyzed the nonosaccharides composition of BSPI-A from Bletilla striata.
3. The means to separate and analyze mixed oligosaccharides using HPL、ESI-MS、LC-ESI-MS was successfully established, which was based on a new reagent 2-Aminoanthraquinone. This method had potential application prospect for the analysis of complicated oligosaccharides of food system.
引文
[1]Rademacher T. W, Parekh R. B, Dwek R. A.. Glycobiology[J]. Annual Review of Biochemistry,1988,57:785-838
[2]田云,卢向阳.糖生物学[J].生物学通报,2002,37(8)：11
[3]金城.糖生物学--破解基因组功能的必由之路[J].中国科学院研究生院学报,2001,18(1)：67-71
[4]Semmes O.. J., Feng Z., Adam B.L., et al. Evaluation of serum protein profiling by surface-enhanced laser desorption/ionization time-of-flight mass spectrometry for the detection of prostate cancer:Ⅰ. Assessment of platform reproducibility[J]. Clin. Chem., 2005,51:102-112
[5]聂赣娟,周建华,李茂玉等.肺鳞癌患者与健康人血清的差异蛋白质组学研究[J].生物化学与生物物理进展,2008,35(3)：349-355
[6]邱惠麒,张稚琴.肿瘤标志物CA125在妇科疾病中的应用[J].浙江预防医学,1999,20(8)：30-31
[7]Sonoda K., Miyamoto S., Hirakawa Toshio, et al. Clinical significance of RCAS1 as a biomarker of uterine cancer [J]. Gynecologic Oncology,2006,103:924-931
[8]Hirabayashi J, Arata Y, Kasai. Glycome project:concept, strategy and preliminary application to Caenorhabditis elegans[J]. Proteomics,2001, 1(2):295-303
[9]Taniguchi N, Ekuni A, Ko J.H, et al. A glycomic approach to the identification and characterization of glycoprotein function in cells transfected with glycosyltransferase genes[J]. Proteomics,2001, 1(2):239-247
[10]Pilobello K. T, Mahal L. K. Deciphering the glycocode:the complexity and analytical challenge of glycomics[J]. Current Opinion in Chemical Biology,2007,11:300-305
[11]金城.糖生物学：基因组学和蛋白质组学的延伸[J].科技前沿与学术评论,2003,23(2)：31-34
[12]王镜岩,朱圣庚,徐长法.生物化学.第三版.北京：高等教育出版社,2002,77-80
[13]Drickamer K, Taylor M. E. Evolving views of protein glycosylation[J]. Trends Biochem. Sci.,1998,23(9):321-324
[14]Dwek R. A. Glycobiology:towards understanding the function of sugars[J]. Biochem. Soc. Trans,1995,23(1):1-25
[15]Lis H, Sharon N. Protein glycosylation. Structural and functional Aspects[J]. Eur. J. Biochem,1993,218(1):1-27
[16]Lowe J. B. Glycan-dependent leukocyte adhesion and recruitment in inflammation[J]. Curr. Opin. Cell Biol,2003,15(5):531-538
[17]Fukuda M. Possible roles of tumor-associated carbohydrate antigens [J]. Cancer Res, 1996,56(10):2237-2244
[18]Lowe J. B, Marth J. D. A genetic approach to Mammalian glycan function[J]. Annu. Rev. Biochem,2003,72:643-691
[19]张真庆.质谱分析外源性和内源性寡糖的方法学研究[D].青岛：中国海洋大学,2006
[20]Olden K. Adhesion molecules and inhibitors of glycosylation in cancer[J]. Semin. Cancer Biol,1993,4(5):269-276
[21]Femenia A, Sanchez E. S, Simal S, Rossello C. Compositional features of polysaccharides from Aloe vera (Aloe barbadensis Miller) plant tissues[J]. Carbohydratepolymers,1999,39(2):109-117
[22]张旭.蛋白质糖基化工程[J].生物工程进展,1995,15(2)：30-35
[23]曹立环.糖链结构不同的纤连蛋白与HT1080细胞结合研究[J].生物化学杂志,1996,12(2)：161-164
[24]刘义辉.胸腺细胞表面岩藻糖化抗原在凋亡过程中变化的初步研究[J].生物化学杂志,1996,12(5)：559-563
[25]Helenius A, Aebi M. Intracellular functions of N-linked glycans[J]. Science,2001, 291(5512):2364-2369
[26]Rudd PM, Elliott T, Cresswell P, et al. Glycosylation and the immune system[J]. Science,2001; 291(5512):2370-2375
[27]Wells L, Vosseller K, Hart GW. Glycosylation of nucleocytoplasmic proteins:signal transduction and O-GlcNAc[J]. Science,2001; 291(5512):2376-2378
[28]Galustion C, ElvissN, Chart H, et al, Interactions of the gastrotropic bacterium Helicobacter pylori with the leukocyte-endothelium adhesion molecules [J], the selectins-a preliminary report. FEMS Immunol Med Microbiol,2003; 36(3):127-134
[29]Kansas G. Selectins and their ligands:current concepts and controversies[J]. Blood, 1996;88(9):3259-3287
[30]Roth J. Prorein N-glycosylation along the secretory pathway:relationship to organelle topography and function, protein quality control and cell interactions [J]. Chem Rev,2002,102(2):285-303
[31]Vacquier V D, Moy G W. The fucose sulfate polymer of egg jelly binds to sperm REJ and is the inducer of the sea urchin sperm acrosome reaction[J]. Dev Biol,1997, 192(1):125-135
[32]Tiemeyer M, Goodman C.S. Gliolectin is a novel carbohydrate-binding protein expressed by a subset of glia in the embryonic Drosophila nervous system[J] Development,1996,122(3):925-936
[33]Brockhausen I, Schutzbach J, Kuhns W. Glycoproteins and their relationship to human disease[J]. Acta Anat,1998,161(1-4):36-78
[34]张旭.蛋白质糖基化工程J].生物工程进展,1995,15(2)：30-35
[35]Hames N M, Hooper J D, Houghton. Instant Notes in Biochemistry. United Kingdom:BIOS Scientific Publishers Limited.1997,225-228
[36]郭玉娜.气相色谱质谱法用于糖类物质结构分析的新方法研究[D].西北大学,2008：1-5
[37]Zhang R, etal. Synthesis and application of fmoc-Hydrazine for the quantitative determination of saccharides by reversed-phase HPLC in the low and subpicomole range[J]. Anal Biochem,1991,195:160-166
[38]王静,王晴,向文盛.色谱法在糖类物质分析中的应用[J].分析化学,2001,29(2)：222-227
[39]Arland T, Hotchkiss J, Kevin B. Isolation of oligogalacturonic acids in gram quantities by preparative HPLC[J]. Carbohydrate Research,1991,215(11):84-90
[40]王晨,田庚元.糖蛋白中糖链的结构研究[J].化学通报,1994,5：8-11
[41]Spiro M. J, Spiro R G. Monosaccharide determination of glycoconjugates by reverse-phase HPLC of the phenylthio carbamyl derivatives[J]. Anal Biochem, 1992,204(1):152-156
[42]Ben-Bassat A A, Grushka E. HPLC of mono-and oligosaccharides[J]. Chromatogr, 1991,14(6):1051-1053
[43]丁玉明,铃木义仁.半微柱液相色谱分离与激光共振拉曼检测法分析果汁中的单糖[J].色谱,1997,15(4)：281-282
[44]将国荣,曹宜,韩泳.紫外检测法在糖类物质分析中的应用[J].苏州大学学报,2003,17(5)：44-45
[45]Fritz J. H, Georld G. Determination of carbohydrates and alochols in wine by HPLC-ion-exchange-chromatography and RI detection[J]. GTI Labor Fachz.1997, 41(9):882,885-886
[46]甘宾宾.高效液相色谱法测定低聚果糖的组分[J].色谱,1999,17(1)：87-89
[47]Vesrari C. A, SPniabelli. U, Galassi S, An improved HPLC method for the analysis of organic acids, carbohydrates, alchols in grape must and wines[J]. LIq. Chromatogr. Relat Techonl,2000,23(13):2047-2065
[48]Mendes E.E, Proensal B, Ferrira M.P, Ferreira M.A. Qualitye valuation of Portuguese honey [J]. CarbohydrPolym,1998,37(3):220-223
[49]朱曙东,赵升皓.氨基酸的高校液相色谱分析[J].色谱,199412(1)
[50]Lee Y. C. High-Performance anion-exchange chromatography for carbohydrate analysis [J]. Anal. Biochem,1990,189:154-160
[51]Marjata K, Tarja T. Residual lignin-carbohydrate complexes from the TCF-bleached pine kraft pulps studied by pyrolysis-GC/MS and chemonetrics[J]. Ind, Carta,1997, 35(4):91-92
[52]孙兴权,李静,耿美玉,等.糖组学研究中糖蛋白糖链结构分析技术[J].化学进展,2007,19(1)
[53]徐瑾,张庆和,王风云.液相色谱荧光分析法在糖类物质中的应用[J].色谱,2003,21(2)：115-116
[54]Davies M J, Hounsell E F. Carbohydrate Chromatography:Towards Yoctomole Sensitivity[J].Biomedical Chromatography 1996,10(6):285-289
[55]Honda S. J Chromatogr A,1996,720(1-2):183
[56]薛向东,王仲孚,黄琳娟,等.基于电喷雾电离质谱(ESI-MS)的苯胺稳定同位素标记对还原性寡糖(链)的定性定量分析方法[J].高等学校化学学报,2010, 31(11)：2173-2180
[57]Spiro M J, Spiro R G. Monosaccharide determination of glycoconjugates by reverse-Phase HPLC of their phenylthiocarbamyl derivatives [J]. Anal Biochem,1992, 204(1):152-154
[58]Yuan C L, Bryan I L, Noboru T, etal. Parameterization of contribution of sugar units to elution volumes in reverse-phase HPLC of 2-pyridylaminated oligosaceharides[J]. Anal.Biochem,1990,188:259-266
[59]Fujimoto I, Menon K K, Otake Y, et al. Systematic analysis of N-linked sugar chains from whole tissue employing partial automation[J]. Anal.Bioehem.1999, 267:336-343
[60]Kevin G R, NorikoT, Yoshihiro N, et al. Quantitative mapping of the A-linked sialyloligosaceharides of recombinant erythropoietin combination of direct high-performance anion-exchange chromatography and 2-amino pyridine derivatization[J]. Anal.Bioehem,1992,206:278-287
[61]Isao H, Yasuhito T. Examination of number-average degree of polymerization and molar-abased distribution of amylase by fiuorescent labeling with 2-aminopyridine[J]. Carbohydrate Res,1996,306:421-426
[62]Rice K G, Takahashi N, Namiki Y, et al. Anal Biochem,1992,206(2):278
[63]Noboru T, Masayasu K, Hideko I. Structural analysis of N-linked oligosaceharides by acombination of glycopeptidase, exoglyeosidases and high-performance liquide chromatography[J]. Anal. Bioehem,1987,163:489-499,
[64]France R R, Cumpstey I, Butters T D, et al. Fluorescence labelling of carbohydrates with 2-aminobenzamide (2AB) [J]. Tetrahedron:Asymmetry,2000, 11(24):4985-4994
[65]Hiroshi K, Akiko K, Kazuyuki S. Microanalysis of glyeoscaminoglyean-derived disaceharides labeled with the fluorophore 2-aminobenzamide acridone by capillary eleetrophoresis and high-performance liquid chromatographs[J]. Anal.Bioehem, 1995,232:114-121
[66]Joanne C, Helen B, Patriek C. Carbohydrate release from picomole quantities of glycoprotein and characterization of glycans by high-performance liquid chromatography and mass spectrometry[J]. J.Chromatogr.B,1999,734:169-174
[67]Poulter L, Karrer R, Burlingame A. L. n-Alkyl p-aminobenzoates as derivatizing agents in the isolation, separation, and characterization of submicrogram quantities of oligosaccharides by liquid secondary ion mass spectrometry[J]. Analytical Biochemistry 1991,195(1):1-13
[68]蒋可,陈宇东,钟晋.高压液相色谱法分离寡糖的对氨基苯甲酸乙酯衍生物[J].生物化学杂志,1993,9(3)：342-346
[69]Murata T, Shibatsuji M, Yoshimi Y, Hara H, Yasuno S, Yamaguchi T, Moriya H, Sweely C, Ikekita M. Res CommunBiochem Cell Mol Biol,1997,1 (4):285
[70]Eggert F M, Jones M. Measurementofneutral sugars in glycoproteins as dansylderivatives by automated high-performance liquid chromatography[J]. J.Chromatogr,1985,333:123-131
[71]朱晓兰,夏文水.甲壳素纯度的高效液相色谱法测定[J].分析测试学,2003,22(4)：9-13
[72]林启山,张任恩,刘国诠.痕量氨基糖和中性单糖的高效毛细管电泳及液相色谱分析[J].色谱,1995,13(1)：12-15
[73]孙清华,刘道杰.用于测定糖的衍生试剂的研究进展[J].化学试剂,2005,27(11)：653-656
[74]周蓉,齐莉,王雅芬,等.甘草多糖的分离纯化及高效毛细管电泳分析[J].分析化学,1999,27(2)：245.
[75]Honda S., Suzuki S., Taga A.. Analysis of carbohydrates as l-phenyl-3-methyl-5-pyrazolone derivatives by capillary/microchip electrophoresis and capillaryelectrochromatography[J]. Journal of Pharmaceutical and Biomedical Analysis, 2003,30:1689-1714
[76]Zhao J.Y, Diedrich P, Zhang Y, et al. Detection of 100 molecules of product formed in a fucosyltransferase reaction[J]. Chromatogr,B,1994,657,307
[77]Nakhla T, Fu D, Zopf D. Neutral oligosaccharide content of preterm human milk[J]. British Journal of Nutrition,1999,269(82):361-367
[78]Zhang L, Zhang X, You J M, et al. Determination of Amines by High Performance Liquid Chromatography with a Pre-column Derivatization and Fluorescence DetectionChin[J]. Anal. Chem,2004,32(2):1002-1010
[79]Strydom. Chromatographic separation of 1-phenyl-3-methyl-5-pyrazolone derivatized neutral,acidic and basic aldoses[J]. Journal of Chromatography A, 1994,678(1):17-23。
[80]Kakehi K, Suzuki S, Honda S, et al. Precolumn labeling of reducing carbohydrates with 1-(p-methoxy)phenyl-3-methyl-5-pyrazolone:Analysis of neutral and sialic acid-containing oligosaccharides found in glycoproteins[J]. Analytical Biochemistry,1991,199(2):256-268
[81]Ynag W, Ming Y D. Analysis of carbohydrates in drinks by high-peorfermance liquid chormoatgraphy with danymically modified amino column and evaporative light scattering detection[J]. J Chromatogr,2000,904:113-117
[82]Mawhinney T P, Chnace D L. Carbohydr. Chem.,1994,13(6):828-838
[83]Bhavanandan V. P. QinZhu, KuazuoYamakami, etl. Glycocojugate [J].1998,15(1):
[84]Ii T, Ohashi Y, Matsuzaki Y, et al. Electrospray mass spectrometry of pentacosasaccharides of blood group activity and related compounds [J]. Organic Mass Spectrometry,1993,28(11):1340-1344
[85]桑志红,杨松成.电喷雾电离质谱及其在蛋白质化学研究中的应用[J].国外医学.医学分册,2000,23(3)：234-236
[86]Ramsay S L, Meikle P J, Hopwood J J. Determination of monosaccharides and disaccharides in mucopolysaccharidoses patients by electrospray ionisation mass spectrometry[J]. Molecular Genetics and Metabolism,2003,78(3):193-204
[87]Wang F, Nakouzi A, Angelett I, et al. Site-specific characterization of the N-linked oligosaccharides of a murine immunoglobulin M by high-performance liquid chromatography/electrospray mass spectrometry [J]. Analytical Biochemistry, 2003,314:266-280.
[88]Read S M, Currie G, Bacic A. Analysis of the structural heterogeneity of laminarin by electrospray-ionisation-mass spectrometry.[J] Carbohydrate Research,1996, 281(2):187-201
[89]Domon B, Costello C E. Coordination of alkali metals to oligosaccharides dictates fragmentation behavior in matrix assisted laser desorption ionization/Fourier transform mass spectrometry.Analytical chemistry,1994,66(5):692-698
[90]Daas P J, Arisz P W, Schols H A, et al. Analysis of Partially Methyl-Esterified Galacturonic Acid Oligomers by High-Performance Anion-Exchange Chromatography and Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry [J]. Analytical Biochemistry.,1998,257(2):195-202
[91]Stahl B, Linos A, Karas M, et al. Analysis of Fructans from Higher Plants by Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry [J].Analytical Biochemistry,1997,246(2):195-204
[92]王仲孚,张英,林雪等.1-苯基-3-甲基-5-吡哗啉酮(PMP)柱前衍生化寡糖链的HPLC分离及其激光解吸电离质谱分析[J].2006,65(23)：2761-2764
[93]Kuster B, Naven T J, Harvey D J.Rapid Approach for Sequencing Neutral Oligosaccharides by exoglycosidase digestion and matrix-assisted laser desorption/Ionization time-of-flight mass spectrometry[J]. Journal of Mass Spectrometry,1996,31(10):1131-1140
[94]叶林,张虹.质谱及色谱-质谱联用技术在多糖结构分析中的应用[J].理化检验-化学分册,2010,46(11)：1355-1359
[95]李蓉,梁恒.生物质谱-蛋白质组研究的关键技术[J].化学通报,2002,11：748-750
[96]Webater J M, Oxley D, Pettolino F A, et al. Characterisation of secreted polysaccharides and (glyco)proteins from suspension cultures of Pyrus communis. Phytochemistry[J],2008,69(4):873-881
[97]王浩,刘艳琴,杨红梅,等.液相色谱-质谱联用技术测定无糖食品中果糖、葡萄糖、蔗糖、麦芽糖和乳糖[J].分析化学研究简报.2010,38(6)：873-8767
[98]郭文,张英,黄琳娟等.高效液相色谱-质谱联用法分析3-氨基-9-乙基咔唑柱前衍生柱前衍生化壳寡糖[J].色谱,2010,28(8)：776-781
[99]Bucior I, Scheuring S, Engel A, et al. Carbohydrate-carbohydrate interaction provides adhesion force and specificity for cellular recognition[J], The Journal of Cell Biology,2004,165(4):529-537
[100]Lamari F N, Kuhn R, Karamano N K. Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis[J], Journal of Chromatography B,2003,793 (2003) 15-36
[101]王仲孚,贺建宇,尉亚辉,等.用于寡糖链分析的HPLC柱前衍生化方法研究进展[J].有机化学,2006,26(5)：592-598
[102]Takemoto H. Microquantitative analysis of neutral and amino sugars as fluorescent pyridylamino derivatives by HPLC[J]. Anal Biochem,1985,15:145
[103]Zhang Ying, HuangLinJuan, WANG Zhong Fu.. A sensitive derivatization method for the determination of the sugar composition after Pre-column reductive amination with3-Amino-9-ethylcarbazole(AEC) by high Performance liquid chromatography[J]., Chinese Journal of Chelulstry,2007,25:1-
[104]Townsend R R, Lipniunas P H, Bigge C, et al. Multimode high performance liquid chromatography of fluorescently labeled oligosaccharides from glycoproteins[J]. Anal. Biochem,1996,239(2):201-207
[105]Anumula K R. Process for immunization and for immobilization onto the sur faces of ELISA plates of an avidinbiotinyl compound complex[J]. Anal. Biochem,1994, 220 (2):275-283.
[106]Meyer A, Raba C, Fischer K. RP-HPLC determination of sugars, amino sugars and uronic acids after derivatization with p-aminobenzoic acid[J]. Anal. Chem,2001, 73(11):2377-2382.
[107]Joanne C, Helen B, Edourd S P, et al. Analysis of oligosaccharides by microbore high-performance liquid chromatography [J]. Anal.Chem.2000,72:1469-1474.
[108]Bardotti A, Ravenscroft N, Rieei S D,et al. Quantitative determination of saccharide in haemophilus infiuenzae type glycoconjugate vaceines, alone and in combination with DPT, by use of high-performance anion-exchange chromatography with pulsed amperometric detection[J]. Vaccine.2000,18(19):1982-1993]
[109]Comunale M.A., Lowman M., Long R.E, et al. Proteomic Analysis of Serum Associated Fucosylated Glycoproteins in the Development of Primary Hepatocellular Carcinoma[J]. Journal of Proteome Research,2006, (5):308-315
[110]Isailovic D, Kurulugama R.T, Plasencia M. D, et al. Profiling of Human Serum Glycans Associated with Liver Cancer and Cirrhosis by IMS-MS[J]. Journal of Proteome Research,2008, (7):1109-1117
[111]Joanne C, Helen B, Patriek C. Carbohydrate release from picomole quantities of glycoprotein and characterization of glycans by high-performance liquid chromatography and mass spectrometry[J]. Chromatogr. B.1999,734:169-173
[112]Toppila S, Paavonen T, Laitinen A, et al. Endothelial sulfated sialyl Lewis X glycans, putative L-selectin ligands, are preferentially expressed in bronchial asthma but not in other chronic inflammatory lung diseases[J]. Am. J. Respir. Cell Mol. Biol.,2000,23:492-498
[113]Robards K, Whitelaw M. Chromatography of monosaccharides and disaccharides[J]. J Chromatogr,1986,373:81-84
[114]蒋秋燕,乔旭光.生命科学的新领域--糖生物学[J].山东农业大学学报(自然科学版).2003,34(2)：294-296
[115]王克夷.正在来临的糖组学[J].生命的化学,2000,20(6)：286-287
[116]陈惠黎.牛津大学糖生物学研究所简介[J].生命的化学,1999,19(3)：109-112
[117]李发美.分析化学[M].北京,人民卫生出版社.2004,443-444
[118]Arland T, Hotchkiss J. Kevin B. Isolation of oligogalacturonic acids in gram quantities by preparative HPLC[J]. Carbohydrate Research,1991,215(11):82-90.
[119]牟世芬,刘克纳.离子色谱方法及应用[M].北京,二化学工业出版社.2000：97-107
[120]金恒亮.高压液相色谱法[M].北京,原子能出版社,1987：59-62
[121]Eggert F M, Jones M. Measurement of neutral sugars in glycoproteins as dansylderivatives by automated high-performance liquid chromatography. J.Chromatogr,1985,333:123-131
[122]Packer N.H, Lawson M. A, Redmond J.W, et al. A general approach to desalting oligosaccharides released from glycoprotein[J]. Glycocojugate,1998,15(8):737-747
[123]王博,徐莎,黄琳娟,等.白芨多糖BSPI-A的分离纯化及结构研究[J].2010,31(17)：120-123
[124]孙达峰,史劲松,张卫明.等,白芨多糖胶研究进展[J].2009,30(3)：296-298
[125]Yang Liyan, Wang Zhongfu, Huang Linjuan. Isolation and structural characterization of a polysaccharide FCAP1 from the fruit of cornus officinalis[J]. carbohydrate Research,2010,20(6):286-287
[126]Zhang Pin, Wang Zhongfu,Xie Mingming. Detection of carbohydrates using a Pre-column derivatization reagent 1-(4-isopropyl)methyl-3-methyl-5-pyrazolone by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry. Journal of Chromatography B,2010,878(2010):1135-1144
[127]Taniguchi N, Honke K, Fukuda M. Handbook of Glycosyltransferases and Related Genes[M]. Springer,2002:1-2
[128]Dwek M.V, Brooks S.A, Harnessing changes in cellular glycosylation in new cancer treatment strategies. Curr. Cancer Drug Targets,2004, (4):425-442
[129]莫琳·E·泰勒,库尔特·德里卡默.糖生物学导论[M].北京,化学工业出版社,2006：26-100
[130]Fernandes B, Sagman U, Auger M. et al. Beta 1-6 branched oligosaccharides as a marker of tumor progression in human breast and colon neoplasia[J]. Cancer Res, 1991,51:718-723
[131]Taniguchi N, Miyoshi E, Ko J.H, et al. Implication of N-acetylglucosaminyl transferases III and V in cancer:gene regulation and signaling mechanism[J]. Biochim. Biophys. Acta,1999,1455:287-300
[132]刘可人,金美芳,吴士良.O-糖基化位点预测及糖基化酶催化特点[J].生命的化学,2006,26(1)：25-27
[133]YODOSHI M, TANI A, OHTA Y, et al. Optimized conditions for high-performance liquid chromatography analysis of oligosaccharides using 7-amino-4-methylcoumarin as a reductive amination reagent[J]. Journal of Chromatography A,2008(2),1203: 137-145.
[134]郭巧玲.低聚壳聚糖的生理活性及应用[J].漳州职业技术学院学报,2008,10(4)：27-29
[2]田云,卢向阳.糖生物学[J].生物学通报,2002,37(8)：11
[3]金城.糖生物学--破解基因组功能的必由之路[J].中国科学院研究生院学报,2001,18(1)：67-71
[4]Semmes O.. J., Feng Z., Adam B.L., et al. Evaluation of serum protein profiling by surface-enhanced laser desorption/ionization time-of-flight mass spectrometry for the detection of prostate cancer:Ⅰ. Assessment of platform reproducibility[J]. Clin. Chem., 2005,51:102-112
[5]聂赣娟,周建华,李茂玉等.肺鳞癌患者与健康人血清的差异蛋白质组学研究[J].生物化学与生物物理进展,2008,35(3)：349-355
[6]邱惠麒,张稚琴.肿瘤标志物CA125在妇科疾病中的应用[J].浙江预防医学,1999,20(8)：30-31
[7]Sonoda K., Miyamoto S., Hirakawa Toshio, et al. Clinical significance of RCAS1 as a biomarker of uterine cancer [J]. Gynecologic Oncology,2006,103:924-931
[8]Hirabayashi J, Arata Y, Kasai. Glycome project:concept, strategy and preliminary application to Caenorhabditis elegans[J]. Proteomics,2001, 1(2):295-303
[9]Taniguchi N, Ekuni A, Ko J.H, et al. A glycomic approach to the identification and characterization of glycoprotein function in cells transfected with glycosyltransferase genes[J]. Proteomics,2001, 1(2):239-247
[10]Pilobello K. T, Mahal L. K. Deciphering the glycocode:the complexity and analytical challenge of glycomics[J]. Current Opinion in Chemical Biology,2007,11:300-305
[11]金城.糖生物学：基因组学和蛋白质组学的延伸[J].科技前沿与学术评论,2003,23(2)：31-34
[12]王镜岩,朱圣庚,徐长法.生物化学.第三版.北京：高等教育出版社,2002,77-80
[13]Drickamer K, Taylor M. E. Evolving views of protein glycosylation[J]. Trends Biochem. Sci.,1998,23(9):321-324
[14]Dwek R. A. Glycobiology:towards understanding the function of sugars[J]. Biochem. Soc. Trans,1995,23(1):1-25
[15]Lis H, Sharon N. Protein glycosylation. Structural and functional Aspects[J]. Eur. J. Biochem,1993,218(1):1-27
[16]Lowe J. B. Glycan-dependent leukocyte adhesion and recruitment in inflammation[J]. Curr. Opin. Cell Biol,2003,15(5):531-538
[17]Fukuda M. Possible roles of tumor-associated carbohydrate antigens [J]. Cancer Res, 1996,56(10):2237-2244
[18]Lowe J. B, Marth J. D. A genetic approach to Mammalian glycan function[J]. Annu. Rev. Biochem,2003,72:643-691
[19]张真庆.质谱分析外源性和内源性寡糖的方法学研究[D].青岛：中国海洋大学,2006
[20]Olden K. Adhesion molecules and inhibitors of glycosylation in cancer[J]. Semin. Cancer Biol,1993,4(5):269-276
[21]Femenia A, Sanchez E. S, Simal S, Rossello C. Compositional features of polysaccharides from Aloe vera (Aloe barbadensis Miller) plant tissues[J]. Carbohydratepolymers,1999,39(2):109-117
[22]张旭.蛋白质糖基化工程[J].生物工程进展,1995,15(2)：30-35
[23]曹立环.糖链结构不同的纤连蛋白与HT1080细胞结合研究[J].生物化学杂志,1996,12(2)：161-164
[24]刘义辉.胸腺细胞表面岩藻糖化抗原在凋亡过程中变化的初步研究[J].生物化学杂志,1996,12(5)：559-563
[25]Helenius A, Aebi M. Intracellular functions of N-linked glycans[J]. Science,2001, 291(5512):2364-2369
[26]Rudd PM, Elliott T, Cresswell P, et al. Glycosylation and the immune system[J]. Science,2001; 291(5512):2370-2375
[27]Wells L, Vosseller K, Hart GW. Glycosylation of nucleocytoplasmic proteins:signal transduction and O-GlcNAc[J]. Science,2001; 291(5512):2376-2378
[28]Galustion C, ElvissN, Chart H, et al, Interactions of the gastrotropic bacterium Helicobacter pylori with the leukocyte-endothelium adhesion molecules [J], the selectins-a preliminary report. FEMS Immunol Med Microbiol,2003; 36(3):127-134
[29]Kansas G. Selectins and their ligands:current concepts and controversies[J]. Blood, 1996;88(9):3259-3287
[30]Roth J. Prorein N-glycosylation along the secretory pathway:relationship to organelle topography and function, protein quality control and cell interactions [J]. Chem Rev,2002,102(2):285-303
[31]Vacquier V D, Moy G W. The fucose sulfate polymer of egg jelly binds to sperm REJ and is the inducer of the sea urchin sperm acrosome reaction[J]. Dev Biol,1997, 192(1):125-135
[32]Tiemeyer M, Goodman C.S. Gliolectin is a novel carbohydrate-binding protein expressed by a subset of glia in the embryonic Drosophila nervous system[J] Development,1996,122(3):925-936
[33]Brockhausen I, Schutzbach J, Kuhns W. Glycoproteins and their relationship to human disease[J]. Acta Anat,1998,161(1-4):36-78
[34]张旭.蛋白质糖基化工程J].生物工程进展,1995,15(2)：30-35
[35]Hames N M, Hooper J D, Houghton. Instant Notes in Biochemistry. United Kingdom:BIOS Scientific Publishers Limited.1997,225-228
[36]郭玉娜.气相色谱质谱法用于糖类物质结构分析的新方法研究[D].西北大学,2008：1-5
[37]Zhang R, etal. Synthesis and application of fmoc-Hydrazine for the quantitative determination of saccharides by reversed-phase HPLC in the low and subpicomole range[J]. Anal Biochem,1991,195:160-166
[38]王静,王晴,向文盛.色谱法在糖类物质分析中的应用[J].分析化学,2001,29(2)：222-227
[39]Arland T, Hotchkiss J, Kevin B. Isolation of oligogalacturonic acids in gram quantities by preparative HPLC[J]. Carbohydrate Research,1991,215(11):84-90
[40]王晨,田庚元.糖蛋白中糖链的结构研究[J].化学通报,1994,5：8-11
[41]Spiro M. J, Spiro R G. Monosaccharide determination of glycoconjugates by reverse-phase HPLC of the phenylthio carbamyl derivatives[J]. Anal Biochem, 1992,204(1):152-156
[42]Ben-Bassat A A, Grushka E. HPLC of mono-and oligosaccharides[J]. Chromatogr, 1991,14(6):1051-1053
[43]丁玉明,铃木义仁.半微柱液相色谱分离与激光共振拉曼检测法分析果汁中的单糖[J].色谱,1997,15(4)：281-282
[44]将国荣,曹宜,韩泳.紫外检测法在糖类物质分析中的应用[J].苏州大学学报,2003,17(5)：44-45
[45]Fritz J. H, Georld G. Determination of carbohydrates and alochols in wine by HPLC-ion-exchange-chromatography and RI detection[J]. GTI Labor Fachz.1997, 41(9):882,885-886
[46]甘宾宾.高效液相色谱法测定低聚果糖的组分[J].色谱,1999,17(1)：87-89
[47]Vesrari C. A, SPniabelli. U, Galassi S, An improved HPLC method for the analysis of organic acids, carbohydrates, alchols in grape must and wines[J]. LIq. Chromatogr. Relat Techonl,2000,23(13):2047-2065
[48]Mendes E.E, Proensal B, Ferrira M.P, Ferreira M.A. Qualitye valuation of Portuguese honey [J]. CarbohydrPolym,1998,37(3):220-223
[49]朱曙东,赵升皓.氨基酸的高校液相色谱分析[J].色谱,199412(1)
[50]Lee Y. C. High-Performance anion-exchange chromatography for carbohydrate analysis [J]. Anal. Biochem,1990,189:154-160
[51]Marjata K, Tarja T. Residual lignin-carbohydrate complexes from the TCF-bleached pine kraft pulps studied by pyrolysis-GC/MS and chemonetrics[J]. Ind, Carta,1997, 35(4):91-92
[52]孙兴权,李静,耿美玉,等.糖组学研究中糖蛋白糖链结构分析技术[J].化学进展,2007,19(1)
[53]徐瑾,张庆和,王风云.液相色谱荧光分析法在糖类物质中的应用[J].色谱,2003,21(2)：115-116
[54]Davies M J, Hounsell E F. Carbohydrate Chromatography:Towards Yoctomole Sensitivity[J].Biomedical Chromatography 1996,10(6):285-289
[55]Honda S. J Chromatogr A,1996,720(1-2):183
[56]薛向东,王仲孚,黄琳娟,等.基于电喷雾电离质谱(ESI-MS)的苯胺稳定同位素标记对还原性寡糖(链)的定性定量分析方法[J].高等学校化学学报,2010, 31(11)：2173-2180
[57]Spiro M J, Spiro R G. Monosaccharide determination of glycoconjugates by reverse-Phase HPLC of their phenylthiocarbamyl derivatives [J]. Anal Biochem,1992, 204(1):152-154
[58]Yuan C L, Bryan I L, Noboru T, etal. Parameterization of contribution of sugar units to elution volumes in reverse-phase HPLC of 2-pyridylaminated oligosaceharides[J]. Anal.Biochem,1990,188:259-266
[59]Fujimoto I, Menon K K, Otake Y, et al. Systematic analysis of N-linked sugar chains from whole tissue employing partial automation[J]. Anal.Bioehem.1999, 267:336-343
[60]Kevin G R, NorikoT, Yoshihiro N, et al. Quantitative mapping of the A-linked sialyloligosaceharides of recombinant erythropoietin combination of direct high-performance anion-exchange chromatography and 2-amino pyridine derivatization[J]. Anal.Bioehem,1992,206:278-287
[61]Isao H, Yasuhito T. Examination of number-average degree of polymerization and molar-abased distribution of amylase by fiuorescent labeling with 2-aminopyridine[J]. Carbohydrate Res,1996,306:421-426
[62]Rice K G, Takahashi N, Namiki Y, et al. Anal Biochem,1992,206(2):278
[63]Noboru T, Masayasu K, Hideko I. Structural analysis of N-linked oligosaceharides by acombination of glycopeptidase, exoglyeosidases and high-performance liquide chromatography[J]. Anal. Bioehem,1987,163:489-499,
[64]France R R, Cumpstey I, Butters T D, et al. Fluorescence labelling of carbohydrates with 2-aminobenzamide (2AB) [J]. Tetrahedron:Asymmetry,2000, 11(24):4985-4994
[65]Hiroshi K, Akiko K, Kazuyuki S. Microanalysis of glyeoscaminoglyean-derived disaceharides labeled with the fluorophore 2-aminobenzamide acridone by capillary eleetrophoresis and high-performance liquid chromatographs[J]. Anal.Bioehem, 1995,232:114-121
[66]Joanne C, Helen B, Patriek C. Carbohydrate release from picomole quantities of glycoprotein and characterization of glycans by high-performance liquid chromatography and mass spectrometry[J]. J.Chromatogr.B,1999,734:169-174
[67]Poulter L, Karrer R, Burlingame A. L. n-Alkyl p-aminobenzoates as derivatizing agents in the isolation, separation, and characterization of submicrogram quantities of oligosaccharides by liquid secondary ion mass spectrometry[J]. Analytical Biochemistry 1991,195(1):1-13
[68]蒋可,陈宇东,钟晋.高压液相色谱法分离寡糖的对氨基苯甲酸乙酯衍生物[J].生物化学杂志,1993,9(3)：342-346
[69]Murata T, Shibatsuji M, Yoshimi Y, Hara H, Yasuno S, Yamaguchi T, Moriya H, Sweely C, Ikekita M. Res CommunBiochem Cell Mol Biol,1997,1 (4):285
[70]Eggert F M, Jones M. Measurementofneutral sugars in glycoproteins as dansylderivatives by automated high-performance liquid chromatography[J]. J.Chromatogr,1985,333:123-131
[71]朱晓兰,夏文水.甲壳素纯度的高效液相色谱法测定[J].分析测试学,2003,22(4)：9-13
[72]林启山,张任恩,刘国诠.痕量氨基糖和中性单糖的高效毛细管电泳及液相色谱分析[J].色谱,1995,13(1)：12-15
[73]孙清华,刘道杰.用于测定糖的衍生试剂的研究进展[J].化学试剂,2005,27(11)：653-656
[74]周蓉,齐莉,王雅芬,等.甘草多糖的分离纯化及高效毛细管电泳分析[J].分析化学,1999,27(2)：245.
[75]Honda S., Suzuki S., Taga A.. Analysis of carbohydrates as l-phenyl-3-methyl-5-pyrazolone derivatives by capillary/microchip electrophoresis and capillaryelectrochromatography[J]. Journal of Pharmaceutical and Biomedical Analysis, 2003,30:1689-1714
[76]Zhao J.Y, Diedrich P, Zhang Y, et al. Detection of 100 molecules of product formed in a fucosyltransferase reaction[J]. Chromatogr,B,1994,657,307
[77]Nakhla T, Fu D, Zopf D. Neutral oligosaccharide content of preterm human milk[J]. British Journal of Nutrition,1999,269(82):361-367
[78]Zhang L, Zhang X, You J M, et al. Determination of Amines by High Performance Liquid Chromatography with a Pre-column Derivatization and Fluorescence DetectionChin[J]. Anal. Chem,2004,32(2):1002-1010
[79]Strydom. Chromatographic separation of 1-phenyl-3-methyl-5-pyrazolone derivatized neutral,acidic and basic aldoses[J]. Journal of Chromatography A, 1994,678(1):17-23。
[80]Kakehi K, Suzuki S, Honda S, et al. Precolumn labeling of reducing carbohydrates with 1-(p-methoxy)phenyl-3-methyl-5-pyrazolone:Analysis of neutral and sialic acid-containing oligosaccharides found in glycoproteins[J]. Analytical Biochemistry,1991,199(2):256-268
[81]Ynag W, Ming Y D. Analysis of carbohydrates in drinks by high-peorfermance liquid chormoatgraphy with danymically modified amino column and evaporative light scattering detection[J]. J Chromatogr,2000,904:113-117
[82]Mawhinney T P, Chnace D L. Carbohydr. Chem.,1994,13(6):828-838
[83]Bhavanandan V. P. QinZhu, KuazuoYamakami, etl. Glycocojugate [J].1998,15(1):
[84]Ii T, Ohashi Y, Matsuzaki Y, et al. Electrospray mass spectrometry of pentacosasaccharides of blood group activity and related compounds [J]. Organic Mass Spectrometry,1993,28(11):1340-1344
[85]桑志红,杨松成.电喷雾电离质谱及其在蛋白质化学研究中的应用[J].国外医学.医学分册,2000,23(3)：234-236
[86]Ramsay S L, Meikle P J, Hopwood J J. Determination of monosaccharides and disaccharides in mucopolysaccharidoses patients by electrospray ionisation mass spectrometry[J]. Molecular Genetics and Metabolism,2003,78(3):193-204
[87]Wang F, Nakouzi A, Angelett I, et al. Site-specific characterization of the N-linked oligosaccharides of a murine immunoglobulin M by high-performance liquid chromatography/electrospray mass spectrometry [J]. Analytical Biochemistry, 2003,314:266-280.
[88]Read S M, Currie G, Bacic A. Analysis of the structural heterogeneity of laminarin by electrospray-ionisation-mass spectrometry.[J] Carbohydrate Research,1996, 281(2):187-201
[89]Domon B, Costello C E. Coordination of alkali metals to oligosaccharides dictates fragmentation behavior in matrix assisted laser desorption ionization/Fourier transform mass spectrometry.Analytical chemistry,1994,66(5):692-698
[90]Daas P J, Arisz P W, Schols H A, et al. Analysis of Partially Methyl-Esterified Galacturonic Acid Oligomers by High-Performance Anion-Exchange Chromatography and Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry [J]. Analytical Biochemistry.,1998,257(2):195-202
[91]Stahl B, Linos A, Karas M, et al. Analysis of Fructans from Higher Plants by Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry [J].Analytical Biochemistry,1997,246(2):195-204
[92]王仲孚,张英,林雪等.1-苯基-3-甲基-5-吡哗啉酮(PMP)柱前衍生化寡糖链的HPLC分离及其激光解吸电离质谱分析[J].2006,65(23)：2761-2764
[93]Kuster B, Naven T J, Harvey D J.Rapid Approach for Sequencing Neutral Oligosaccharides by exoglycosidase digestion and matrix-assisted laser desorption/Ionization time-of-flight mass spectrometry[J]. Journal of Mass Spectrometry,1996,31(10):1131-1140
[94]叶林,张虹.质谱及色谱-质谱联用技术在多糖结构分析中的应用[J].理化检验-化学分册,2010,46(11)：1355-1359
[95]李蓉,梁恒.生物质谱-蛋白质组研究的关键技术[J].化学通报,2002,11：748-750
[96]Webater J M, Oxley D, Pettolino F A, et al. Characterisation of secreted polysaccharides and (glyco)proteins from suspension cultures of Pyrus communis. Phytochemistry[J],2008,69(4):873-881
[97]王浩,刘艳琴,杨红梅,等.液相色谱-质谱联用技术测定无糖食品中果糖、葡萄糖、蔗糖、麦芽糖和乳糖[J].分析化学研究简报.2010,38(6)：873-8767
[98]郭文,张英,黄琳娟等.高效液相色谱-质谱联用法分析3-氨基-9-乙基咔唑柱前衍生柱前衍生化壳寡糖[J].色谱,2010,28(8)：776-781
[99]Bucior I, Scheuring S, Engel A, et al. Carbohydrate-carbohydrate interaction provides adhesion force and specificity for cellular recognition[J], The Journal of Cell Biology,2004,165(4):529-537
[100]Lamari F N, Kuhn R, Karamano N K. Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis[J], Journal of Chromatography B,2003,793 (2003) 15-36
[101]王仲孚,贺建宇,尉亚辉,等.用于寡糖链分析的HPLC柱前衍生化方法研究进展[J].有机化学,2006,26(5)：592-598
[102]Takemoto H. Microquantitative analysis of neutral and amino sugars as fluorescent pyridylamino derivatives by HPLC[J]. Anal Biochem,1985,15:145
[103]Zhang Ying, HuangLinJuan, WANG Zhong Fu.. A sensitive derivatization method for the determination of the sugar composition after Pre-column reductive amination with3-Amino-9-ethylcarbazole(AEC) by high Performance liquid chromatography[J]., Chinese Journal of Chelulstry,2007,25:1-
[104]Townsend R R, Lipniunas P H, Bigge C, et al. Multimode high performance liquid chromatography of fluorescently labeled oligosaccharides from glycoproteins[J]. Anal. Biochem,1996,239(2):201-207
[105]Anumula K R. Process for immunization and for immobilization onto the sur faces of ELISA plates of an avidinbiotinyl compound complex[J]. Anal. Biochem,1994, 220 (2):275-283.
[106]Meyer A, Raba C, Fischer K. RP-HPLC determination of sugars, amino sugars and uronic acids after derivatization with p-aminobenzoic acid[J]. Anal. Chem,2001, 73(11):2377-2382.
[107]Joanne C, Helen B, Edourd S P, et al. Analysis of oligosaccharides by microbore high-performance liquid chromatography [J]. Anal.Chem.2000,72:1469-1474.
[108]Bardotti A, Ravenscroft N, Rieei S D,et al. Quantitative determination of saccharide in haemophilus infiuenzae type glycoconjugate vaceines, alone and in combination with DPT, by use of high-performance anion-exchange chromatography with pulsed amperometric detection[J]. Vaccine.2000,18(19):1982-1993]
[109]Comunale M.A., Lowman M., Long R.E, et al. Proteomic Analysis of Serum Associated Fucosylated Glycoproteins in the Development of Primary Hepatocellular Carcinoma[J]. Journal of Proteome Research,2006, (5):308-315
[110]Isailovic D, Kurulugama R.T, Plasencia M. D, et al. Profiling of Human Serum Glycans Associated with Liver Cancer and Cirrhosis by IMS-MS[J]. Journal of Proteome Research,2008, (7):1109-1117
[111]Joanne C, Helen B, Patriek C. Carbohydrate release from picomole quantities of glycoprotein and characterization of glycans by high-performance liquid chromatography and mass spectrometry[J]. Chromatogr. B.1999,734:169-173
[112]Toppila S, Paavonen T, Laitinen A, et al. Endothelial sulfated sialyl Lewis X glycans, putative L-selectin ligands, are preferentially expressed in bronchial asthma but not in other chronic inflammatory lung diseases[J]. Am. J. Respir. Cell Mol. Biol.,2000,23:492-498
[113]Robards K, Whitelaw M. Chromatography of monosaccharides and disaccharides[J]. J Chromatogr,1986,373:81-84
[114]蒋秋燕,乔旭光.生命科学的新领域--糖生物学[J].山东农业大学学报(自然科学版).2003,34(2)：294-296
[115]王克夷.正在来临的糖组学[J].生命的化学,2000,20(6)：286-287
[116]陈惠黎.牛津大学糖生物学研究所简介[J].生命的化学,1999,19(3)：109-112
[117]李发美.分析化学[M].北京,人民卫生出版社.2004,443-444
[118]Arland T, Hotchkiss J. Kevin B. Isolation of oligogalacturonic acids in gram quantities by preparative HPLC[J]. Carbohydrate Research,1991,215(11):82-90.
[119]牟世芬,刘克纳.离子色谱方法及应用[M].北京,二化学工业出版社.2000：97-107
[120]金恒亮.高压液相色谱法[M].北京,原子能出版社,1987：59-62
[121]Eggert F M, Jones M. Measurement of neutral sugars in glycoproteins as dansylderivatives by automated high-performance liquid chromatography. J.Chromatogr,1985,333:123-131
[122]Packer N.H, Lawson M. A, Redmond J.W, et al. A general approach to desalting oligosaccharides released from glycoprotein[J]. Glycocojugate,1998,15(8):737-747
[123]王博,徐莎,黄琳娟,等.白芨多糖BSPI-A的分离纯化及结构研究[J].2010,31(17)：120-123
[124]孙达峰,史劲松,张卫明.等,白芨多糖胶研究进展[J].2009,30(3)：296-298
[125]Yang Liyan, Wang Zhongfu, Huang Linjuan. Isolation and structural characterization of a polysaccharide FCAP1 from the fruit of cornus officinalis[J]. carbohydrate Research,2010,20(6):286-287
[126]Zhang Pin, Wang Zhongfu,Xie Mingming. Detection of carbohydrates using a Pre-column derivatization reagent 1-(4-isopropyl)methyl-3-methyl-5-pyrazolone by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry. Journal of Chromatography B,2010,878(2010):1135-1144
[127]Taniguchi N, Honke K, Fukuda M. Handbook of Glycosyltransferases and Related Genes[M]. Springer,2002:1-2
[128]Dwek M.V, Brooks S.A, Harnessing changes in cellular glycosylation in new cancer treatment strategies. Curr. Cancer Drug Targets,2004, (4):425-442
[129]莫琳·E·泰勒,库尔特·德里卡默.糖生物学导论[M].北京,化学工业出版社,2006：26-100
[130]Fernandes B, Sagman U, Auger M. et al. Beta 1-6 branched oligosaccharides as a marker of tumor progression in human breast and colon neoplasia[J]. Cancer Res, 1991,51:718-723
[131]Taniguchi N, Miyoshi E, Ko J.H, et al. Implication of N-acetylglucosaminyl transferases III and V in cancer:gene regulation and signaling mechanism[J]. Biochim. Biophys. Acta,1999,1455:287-300
[132]刘可人,金美芳,吴士良.O-糖基化位点预测及糖基化酶催化特点[J].生命的化学,2006,26(1)：25-27
[133]YODOSHI M, TANI A, OHTA Y, et al. Optimized conditions for high-performance liquid chromatography analysis of oligosaccharides using 7-amino-4-methylcoumarin as a reductive amination reagent[J]. Journal of Chromatography A,2008(2),1203: 137-145.
[134]郭巧玲.低聚壳聚糖的生理活性及应用[J].漳州职业技术学院学报,2008,10(4)：27-29