万古霉素手性膜拆分D,L-苯甘氨酸及手性拆分机理

doi:10.7503/cjcu20160460

高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (11): 1960.doi: 10.7503/cjcu20160460

万古霉素手性膜拆分D,L-苯甘氨酸及手性拆分机理

袁黎明(), 苏莹秋, 段爱红, 郑莹, 艾萍, 谌学先

云南师范大学化学化工学院, 昆明 650500

收稿日期:2016-06-30 出版日期:2016-11-10 发布日期:2016-10-19
作者简介:联系人简介: 袁黎明, 男, 博士, 教授, 主要从事手性分离方面的研究. E-mail: yuan_limingpd@126.com
基金资助:
国家自然科学基金(批准号: 21365025, 21265026, 21165022)资助

Optical Resolution of D,L-Phenylglycine and Chiral Separation Mechanism Using an Enantioselective Membrane of Vancomycin^†

YUAN Liming^*(), SU Yingqiu, DUAN Aihong, ZHENG Ying, AI Ping, CHEN Xuexian

Faculty of Chemisty and Chemical Engineering, Yunnan Normal University, Kunming 650500, China

Received:2016-06-30 Online:2016-11-10 Published:2016-10-19
Contact: YUAN Liming E-mail:yuan_limingpd@126.com
Supported by:
† Supported by the National Natural Science Foundation of China(Nos.21365025, 21265026, 21165022)

摘要/Abstract

摘要：

以万古霉素和1,6-己二异腈酸酯为单体, 通过界面聚合法在聚砜基膜上制备了万古霉素手性高分子膜. 利用红外光谱及扫描电子显微镜对该膜进行了表征. 将其用于青霉素及头孢菌素类药物的重要中间体苯甘氨酸的手性拆分, 通过优化单体摩尔比、界面聚合时间及外消旋体溶液浓度等分离参数, 可达到超过70%的D-苯甘氨酸对映体过剩值的手性分离. 通过比较研究手性膜吸附、固相萃取、膜色谱、膜渗析和膜超滤过程, 发现手性膜上优先吸附的对映体L-苯甘氨酸并不是各种模式下优先透过的对映体, 结合外消旋体的缔合特性, 提出了“吸附-缔合-扩散”的手性膜分离机理.

关键词: 万古霉素, D, L-苯甘氨酸, 手性膜, 分离机理

Abstract:

Using vancomycin and 1,6-diisocyanatohexane as the monomers, an enantioselective composite membrane was prepared by interfacial polymerization on a polysulfone support and was analyzed by Fourier transform infrared spectroscopy and scanning electron microscopy. The composite membrane was used for enantioseparation of D,L-phenylglycine which is an indispensable reagent in the syntheses of penicillins and cephalosporins. By optimizing the molar ratio of vancomycin and 1,6-diisocyanatohexane, the time of polymerization and the feed concentration of the racemate, an enantiomeric excess[e.e.(%)] of over 70% D-phenylglycine could be obtained. Comparing the membrane adsorption, solid extraction, membrane chromatography, dialysis and ultrafiltration of vancomycin optical resolution membrane, the L-phenylglycine was prior adsorbed, while, the D-phenylglycine was first permeated the membrane. Based on the association characteristic of racemate of D,L-phenylglycine, we suggested, in the first time, that the enantioseparation mechanism of membrane was “adsorption-association-diffusion”.

Key words: Vancomycin, D, L-Phenylglycine, Optical resolution membrane, Enantioseparation mechanism

TrendMD:

袁黎明, 苏莹秋, 段爱红, 郑莹, 艾萍, 谌学先. 万古霉素手性膜拆分D,L-苯甘氨酸及手性拆分机理. 高等学校化学学报, 2016, 37(11): 1960.

YUAN Liming, SU Yingqiu, DUAN Aihong, ZHENG Ying, AI Ping, CHEN Xuexian. Optical Resolution of D,L-Phenylglycine and Chiral Separation Mechanism Using an Enantioselective Membrane of Vancomycin^†. Chem. J. Chinese Universities, 2016, 37(11): 1960.

图/表 8

Fig.1 FTIR spectra of vancomycin(a) and vancomycin membrane(b)

Fig.2 SEM images of top surface(A,C) and cross-section(B,D) of polysulfone membrane(A,B) and enantioselective composite membrane(C,D)

Fig.3 Enantiomeric excess[e.e.(%)] at different molar ratios of 1,6-diisocyanatohexane to vancomycin

Fig.4 Enantiomeric excess[e.e.(%)] at different time of interfacial polymerization

Fig.5 Enantiomeric excess[e.e.(%)] at different feed concentrations

Fig.6 Membrane chromatogram of D,L-phenylglycine

Fig.7 Single crystal structure of D,L-phenylglycine

Scheme 1 Chiral separation mechanism of the “adsorption-association-diffusion” in optical resolution of membrane

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万古霉素手性膜拆分D,L-苯甘氨酸及手性拆分机理

Optical Resolution of D,L-Phenylglycine and Chiral Separation Mechanism Using an Enantioselective Membrane of Vancomycin^†

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万古霉素手性膜拆分D,L-苯甘氨酸及手性拆分机理

Optical Resolution of D,L-Phenylglycine and Chiral Separation Mechanism Using an Enantioselective Membrane of Vancomycin†

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Optical Resolution of D,L-Phenylglycine and Chiral Separation Mechanism Using an Enantioselective Membrane of Vancomycin^†