Effect of the Chiral Selective Reagents-β-Cyclodextrin and Vancomycin-on the Enantiomeric Migration Order of Amino Acids
摘 要
用毛细管电泳法分别在由两种手性选择试剂,β-环糊精(β-CD)和万古霉素(VMC)所组成的分离体系中,研究了19种氨基酸的衍生物的对映异构体的迁移顺序(EMO)。单一β-CD分离体系由含有不同浓度的β-CD的硼酸盐缓冲溶液组成;二元分离体系由不同浓度比例的β-CD和脱氧牛黄胆酸钠溶液所组成,各溶液的pH值为9.5。单一VMC分离体系含2 mmol·L-1 VMC缓冲溶液(pH 7.2);二元VMC分离体系由浓度均为2 mmol·L-1 VMC溶液和海美溴铵溶液组成(pH 7.2)。19种氨基酸须先与芴甲氧羰基氯反应使衍生化。结果表明:各氨基酸的对映体在相同或不同的分离体系中的EMO不一致,特别是在二元VMC体系中,氨基酸的EMO完全发生逆转。据此认为,对于目标氨基酸对映体的分离,可通过用不同的手性分离体系来实现。
Abstract
Capillary electrophoresis (CE) was applied to the study on enantiomeric migration order (EMO) of derivatives of 19 amino acids in separation systems containing the chiral selective reagents, β-cyclodextrin (β-CD) or vancomycin (VMC). Unitary β-CD separation systems were composed of β-CD in various concentrations in solutions buffered at pH 9.5 with borax buffer solution; and binary β-CD systems were composed of β-CD and sodium deoxytaurocholate in various concentration ratios, with pH values of 9.5. Unitary VMC separation system was composed of 2 mmol·L-1 VMC in borate buffer solution of pH 7.2. Binary VMC system was composed of 2 mmol·L-1 VMC and 2 mmol·L-1 HDB in borate buffer solution of pH 7.2. The 19 amino acids should be pre-derivatized with fluorenylmethoxycarbonylchlor and the derivatives were used for CE. It was found that different EMD′s were obtained for the enantiomers amino acids, and especially in the binary VMC system, EMO′s for the derivatives of amino acids were entirely reversed. Hence, separation of enantiomers of any target amino acid could be realized by using an appropriate chiral separation system.
中图分类号 O657.8
所属栏目 工作简报
基金项目 国家自然科学基金(81001595);中央高校基本科研业务费专项资金中央民族大学自主科研项目(0910KYQN67)
收稿日期 2011/7/9
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联系人作者申刚义(sgy@iccas.ac.cn)
备注申刚义(1976-),男,山西长治人,博士,副教授,主要从事色谱分析及生物传感方法研究。
引用该论文: SHEN Gang-yi,SHE Dong-lai,YU Wan-ting,GAO Yan. Effect of the Chiral Selective Reagents-β-Cyclodextrin and Vancomycin-on the Enantiomeric Migration Order of Amino Acids[J]. Physical Testing and Chemical Analysis part B:Chemical Analysis, 2012, 48(11): 1292~1295
申刚义,佘东来,于婉婷,高妍. 手性选择试剂环糊精与万古霉素对氨基酸对映异构体迁移顺序的影响[J]. 理化检验-化学分册, 2012, 48(11): 1292~1295
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参考文献
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【2】YUAN Zhuo-bin, YANG Li-li, ZHANG Shu-sheng. Enantiomeric separation of amino acids by copper(Ⅱ)-L-arginnie ligand exchange capillary zone electrophoresis[J]. Electrophoresis, 1999,20:1842-1845.
【3】QI Li, QIAO Juan, YANG Geng-liang, et al. Enantiomeric separation of alanyl and leucyl dipeptides by capillary electrophoresis with cyclodextrins as chiral selectors[J]. Electrophoresis, 2009,30:2266-2272.
【4】SB F, SNGER-VAN C E, SCRIBA G K E. Enantiomeric separation of alanyl and leucyl dipeptides by capillary electrophoresis with cyclodextrins as chiral selectors[J]. Electrophoresis, 2003,24:1069-1076.
【5】SNGER-VAN C E. Enantiomeric separation of glycyl dipeptides by capillary electrophoresis with cyclodextrins as chiral selectors[J] Electrophoresis, 2000,21:2397-2404.
【6】SNGER-VAN C E. Enantiomeric separation of glycyl dipeptides by capillary electrophoresis with cyclodextrins as chiral selectors[J]. Electrophoresis, 1999,20:3417-3423.
【7】VIGH G, SOKOLOWSKI A D. Capillary electrophoretic separations of enantiomers using cyclodextrin-containing background electrolytes[J]. Electrophoresis, 1997,18:2305-2310.
【8】FANALI S. Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors[J]. J Chromatogr A, 2000,875:89-122.
【9】FILLET M, HUBERT P, CROMMEN J. Enantiomeric separations of drugs using mixtures of charged and neutral cyclodextrins[J]. J Chromatogr A, 2000,875:123-134.
【10】ARMSTRONG D W, TANG Tu-bing, CHEN Shu-shi, et al. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography[J]. Anal Chem, 1994,66:1473-1484.
【11】ARMSTRONG D W, RUNDLETT K L, CHEN J R. Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis[J]. Chirality, 1994,6:496-509.
【12】KANG Jing-wu, BISCHOFF D, JIANG Zheng-jin, et al. A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. dimerization and enantioselectivity[J]. Anal Chem, 2004,76:2387-2392.
【13】KANG Jing-wu, WISTUBA D, SCHURIG V. Fast enantiomeric separation with vancomycin as chiral additive by co-electroosmotic flow capillary electrophoresis: Increase of the detection sensitivity by the partial filling technique[J]. Electrophoresis, 2003,24:2674-2679.
【14】GASPER M P, BERTHOD A, NAIR U B, et al. pH-Dependence of complexation constants and compleex mobility in capillary electrophoresis separations of dipeptide enantiomers[J]. Anal Chem, 1996,68:2501-2514.
【15】康经武,梁冰,陆豪杰,等.以万古霉素为手性选择剂的氨基酸对映体的毛细管电泳快速分离[J].分析化学, 1999,27(4):448-452.
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