河北师范大学学报—

期刊信息

刊名：河北师范大学学报（自然科学版）Journal of Hebei Normal University (Natural Science)
主办：河北师范大学
ISSN： 1000-5854
CN： 13-1061/N
中国科技核心期刊
中国期刊方阵入选期刊
中国高校优秀科技期刊
华北优秀期刊
河北省优秀科技期刊

协同采编系统

友情链接

高效液相色谱中的蛋白质手性固定相

穆惠英^1,2

敦惠娟¹

苗凤智³

魏雨¹

1. 河北师范大学化学与材料科学学院, 河北石家庄 050016;
2. 河北化工医药职业技术学院化学与环境工程系, 河北石家庄 050026;
3. 河北科技大学环境科学与工程学院, 河北石家庄 050018
DOI：

Protein-based Chiral Stationary Phase for High-performance Liquid Chromatography Enantioseparations

MU Hui-ying^1,2, DUN Hui-juan¹, MIAO Feng-zhi³, WEI Yu¹

PDF
下载
HTML

摘要/Abstract

摘要：

对近年来报道的各种高效液相色谱蛋白质手性固定相的研究进行了综述.主要介绍了蛋白质手性固定相的制备、分类、组成、性质、拆分机理及其应用,讨论了各类蛋白质手性固定相的优缺点,指出了目前存在的问题和今后的研究方向.

Abstract：

The enantioseparations of various compounds using proteins as the chiral selectors in high-performance liquid chromatography (HPLC) were considered. The recent development in the classification,the preparation,the properties,the chiral recognition mechanism and the applications of chiral stationary phases used in high performance liquid chromatography were int roduced. The advantages and disadvantages of different chiral stationary phases were also discussed. The problems at present, the research direction and focus for the future have been put forward.

关键词

关键词： 高效液相色谱 ; 蛋白质固定相 ; 手性拆分

Key words： HPLC ; protein2based chiral stationary phase ; chiral resolution

参考文献 39

[1] 孙毓庆. 现代色谱法及其在医药中的应用[M]. 北京:人民卫生出版社,1998 :11.
[2] 陈立仁,蒋生祥,刘霞. 高效液相色谱基础与实践[M]. 北京:科学出版社,2001 :171-191.
[3] 邹汉法. 高效液相色谱法[M]. 北京:科学出版社,1998 :11.
[4] HERMANSSON J. Direct Liquid Chromatographic Resolution of Racemic Drugs Using α₁-acid Glycoprotein As the Chiral Stationary Phase [J]. J Chromatogr,1983,269 (2) :71280.
[5] HAGINAKA J,MATSUNAGA H. Separation of Enantiomers on HPLC Chiral Stationary Phases Based on Human Plasma Al2 pha12acid Glycoprotein :Effect of Sugar Moiety on Chiral Recognition Ability [J]. Enantiomer,2000,5 (1) :37245.
[6] DOMENICI E,BRETT C,SALVADORI P,et al. Synthesis and Chromatographic Properties of an HPLC Chiral Stationary Phase Based Upon Human Serum Albumin [J]. Chromatographia,1990,29 (324) :170-176.
[7] ALL ENMARK S,BOMGREN B,BORÉN H. Optical Resolution of a Series of N-Aroyl D, L-amino Acids by HPLC on Bovine Serum Albumin Covalently Bound to Silica [J]. J Chromatogr A,1983,264 :63-68.
[8] MIWA T, ICHIKAWA M, TSUNO M,et al. Separation Agent for Optical Isomers,Process for Preparing It and Use Thereof [J]. Chem Pharm Bull,1987,35 (2) :682-686.
[9] HENRIKSSON H,MUNOZ I G, ISAKSSON R,et al. Cellobiohydrolase 58 (P. c. Cel 7D) is Complementary to the Homologous CBH I (T. r. Cel 7A) in Enantioseparations [J]. J Chromatogr A,2000,898 (1) :63-74.
[10] MARL E I,ERLANDSSON P,HANSSON L,et al. Separation of Enantiomers Using Cellulase (CBH I) Silica As a Chiral Stationary Phase [J]. J Chromatogr,1991,586 (2) :233-248.
[11] HAGINAKA J,MURASHIMA T,SEYAMA C. Separation of Enantiomers on a Lysozyme2bonded Silica Column [J]. J Chromatogr A,1994,666 (122) :203-210.
[12] MANSUR H S,LOBATO Z P. Surface Functionalization of Porous Glass Networks : Effects on Bovine Serum Albumin and Porcine Insulin Immobilization Biomacromolecules [J]. 2000,1 (4) :789-797.
[13] 于世林. 亲和色谱方法及应用[M]. 北京:化学工业出版社,2008 :145-178.
[14] 徐荣来,杨同华,董伟. 聚N2异丙基丙烯酰胺硅胶键合固定相的制备与评价[J]. 色谱,2008,26 (2) :246-249.
[15] 蒋生祥,刘霞. 硅胶基质高效液相色谱固定相[J]. 色谱,2007,25 (2) :163-173.
[16] MILLOT M C. Separation of Drug Enantiomers by Liquid Chromatography and Capillary Electrophoresis,Using Immobilized Proteins As Chiral Selectors [J]. J Chromatogr B,2003,797 (122) :131-159.
[17] 夏炎,杨万龙,左育民. 锆胶基质阳离子色谱柱填料的制备[J]. 分析化学,2006,34 (4) :511-513.
[18] 魏明星,姚金水,王晓东,等. 高效液相色谱手性聚合物固定相的研究与进展[J]. 高分子通报,2006,10 :23-28.
[19] ENQUIST M,HERMANSSON J. Influence of Uncharged Mobile Phase Additive on Retention and Enantioselectivity of Chiral Drugs Using an Alpha 1-acid Glycoprotein Column [J]. J Chromatogr,1990,519 (2) :271-283.
[20] PINKERTON C,HOWE WJ,URL ICH E L,et al. Protein Binding Chiral Discrimination of HPLC Stationary Phases Made with Whole,Fragmented,and Third Domain Turkey Ovomucoid [J]. Anal Chem,1995,67 (14) :2354-2367.
[21] HAGINAKA J. YAKU GAKU Z. Development of HPLC Packing Materials for Drug Analysis and Their Applications [J]. Nihon Yakugakkai,1996,116 (6) :473-490.
[22] HAGINAKA J,MATSUNAGA H,KAKEHI K. Separation of Enantiomers on a Chiral Stationary Phase Based on Ovoglycoprotein VIII. Chiral Recognition Ability of Partially and Completely Deglycosylated Ovoglycoprotein [J]. J Chromatogr : Biomed Sci Appl,2000,745 (1) :149-157.
[23] WAL KER M,STEVENS L,DUNCAN D,et al. A Comparative Study of the Structure of Egg2white Riboflavin Binding Protein from the Domestic Fowl and Japanese Quail [J]. Comp Biochem Physiol,1991,100 (1) :77-81.
[24] MASSOL INI G,LORENZI D E. Chromatographic Investigation on the Binding Site Characteristics of Quail Egg2white Riboflavin Binding Protein As a Chiral Stationary Phase [J]. J Chromatogr B :Biomed Sci Appl,2000,738 (2) :343-355.
[25] DIVNE C,STAHLBERGJ,TEERI T,et al. High2resolution Crystal Structures Reveal How a Cellulose Chain Is Bound in the 50 ! Long Tunnel of Cellobiohydrolase I from Trichoderma Reesei [J]. J Mol Biol,1998,275 (2) :309-325.
[26] HAGINAKA J,MIYANO Y. Separation of Enantiomers on a Chiral Stationary Phase Based on Pepsin II : Stabilization by a Mixed Protein Phase with Chicken Ovomucoid [J]. Anal Sci,1996,12 (5) :727-732.
[27] HAGINAKA J,MIYANO Y,SAIZEN Y,et al. Separation of Enantiomers on a Pepsin-bonded Column [J]. J Chromatogr A, 1995,708 (1) :161-168.
[28] KARLSSON A,ASPEGREN A. Enantiomeric Separation of Amino Alcohols on Protein Phases Using Statistical Experimental Design A Comparative Study [J]. J Chromatogr A,2000,866 (1) :15-23.
[29] HAGE D S,NOCTOR T A G,WAINER I W. Characterization of the Protein Binding of Chiral Drugs by High-performance Affinity Chromatography Interactions of R- and S-ibuprofen with Human Serum Albumin [J]. J Chromatogr A,1995,693 (1) :23-32.
[30] ALL ENMARK S. Optical Resolution by Liquid Chromatography on Immobilized Bovine Serum Albumin [J]. J Liq Chromatogr,1986,9 (223) :425-442.
[31] JADAUD P,THELOHAN S,SCHONBAUM G R,et al. The Stereochemical Resolution of Enantiomeric Free and Derivatized Amino Acids Using an HPLC Chiral Stationary Phase Based on Immobilized Alpha2chymotrypsin :Chiral Separation Due to Solute Structure or Enzyme Activity [J]. Chirality,1989,1 (1) :38-44.
[32] GYIMESI F K,SZASZ G,GERGEL Y A,et al. Optical Resolution of a Series of Potential Cholecystokinin Antagonist 4 (3H)- quinazolone Derivatives by Chiral Liquid Chromatography on Alpha12acid Glycoprotein Stationary Phase [J]. J Chromatogr Sci,2000,38 (10) :430-434.
[33] KATO I,SCHRODE J,KOHR W J,et al. Chicken Ovomucoid :Determination of Its Amino Acid Sequence,Determination of the Trypsin Reactive Site,and Preparation of All Three of Its Domains [J].Biochemistry,1987,26 (1) :193-201.
[34] ODA Y,MANO N,ASAKAWA N,et al. Comparison of Avidin and Ovomucoid As Chiral Selectors for the Resolution of Drug Enantiomers by High-performance Liquid Chromatography [J]. Anal Sci,1993,9 (2) :221-228.
[35] MUNRO J S,GORML EYJ P,WAL KER T A. Bupropion Hydrochloride : The Development of a Chiral Separation Using a Chiral AGP Column [J]. J Liq Chrom Rel Technol,2001,24 (3) :327-339.
[36] MILLOT M C,SEBILL E B,MANGIN. Enantiomeric Properties of Human Albumin Immobilized on Porous Silica Supports Coated with Polymethacryloyl Chloride [J]. C J Chromatogr A,1997,776 (1) :37-44.
[37] WAINER I W,JADAUD P,SCHOMBAUM G R,et al. Enzymes As HPLC Stationary Phases for Chiral Resolutions : Initial Investigations with α-chymotrypsin [J]. Chromatographia,1988,25 (10) :903-907.
[38] STEWART K K,DOHERTY R F. Resolution of D, L-tryptophan by Affinity Chromatography on Bovine2serum Albuminagarose Columns [J]. Proc Natl Acad Sci USA,1973,70 (10) :2850-2852.
[39] HERMANSSOR J. Direct Liquid Chromatographic Resolution of Racemic Drugs Using Glycoprotein As the Chiral Stationary Phase [J]. J Chromatogr,1983,269 (1) :71-80.