利用L-半胱氨酸自组装膜和混合溶剂协同作用手性拆分DL-谷氨酸

doi:10.7503/cjcu20160866

高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (6): 1076.doi: 10.7503/cjcu20160866

利用L-半胱氨酸自组装膜和混合溶剂协同作用手性拆分DL-谷氨酸

周心慧, 王海水()

华南理工大学化学与化工学院, 广州 510640

收稿日期:2016-12-02 出版日期:2017-06-10 发布日期:2017-05-08
作者简介:联系人简介: 王海水, 男, 博士, 教授, 博士生导师, 主要从事晶体方面的研究. E-mail: wanghsh@scut.edu.cn
基金资助:
国家自然科学基金(批准号: 20873136)和高校科研专项项目(批准号: 2015ZM050)资助.

Co-effect of L-Cysteine Self-assembled Monolayers and Mixed Solvents on Chiral Separation of DL-glutamic Acid^†

ZHOU Xinhui, WANG Haishui^*()

School of Chemistry & Chemical Engineering, South China University of Technology, Guangzhou 510640, China

Received:2016-12-02 Online:2017-06-10 Published:2017-05-08
Contact: WANG Haishui E-mail:wanghsh@scut.edu.cn
Supported by:
† Supported by the National Natural Science Foundation of China(No.20873136) and the Fundamental Research Funds for the Central Universities, China(No.2015ZM050).

摘要/Abstract

摘要：

基于L-半胱氨酸(L-Cys)自组装膜(SAMs)在乙醇-水混合溶剂体系中对外消旋谷氨酸展现出的手性识别能力, 在含60%(体积分数)乙醇的乙醇-水混合溶剂中, 利用L-Cys SAMs对不同手性谷氨酸的选择性结晶作用, 通过多次重结晶, 分离出纯D-谷氨酸晶体, 从而实现了对DL-谷氨酸的手性拆分.

关键词: 手性拆分, 谷氨酸, 乙醇-水混合溶剂, 自组装膜, L-半胱氨酸

Abstract:

In general, crystallization of a racemic glutamic acid aqueous solution will yield optically inactive racemic compound crystals(DL-crystals), it makes a great challenge to chiral separation of DL-glutamic acid. We found that D-crystals and L-crystals(the conglomerates) of glutamic acid can be deposited from the mixed solvents of water and ethanol, providing an opportunity to separate the D- and L-forms of glutamic acid. Moreover, L-cysteine self-assembled monolayers(L-Cys SAMs) on the gold(111) surface showed chiral discriminating ability in the mixed solvents. SEM, XRD and Raman techniques were employed to characterize the crystals grown on the L-Cys SAMs. The relative contents of L-forms and D-forms in the conglomerates were measured by a pre-column derivatization HPLC method. The experimental results demonstrated that the conglomerates with D-glutamic acid excess were obtained on the L-Cys SAMs from a 60%(volume fraction) ethanol-water mixed solvent. And more importantly, the pure D-crystals alone can be deposited from the mixed solvents by the co-effect of L-Cys SAMs and mixed solvents and a typical “in-series enriched method”.

Key words: Chiral separation, Glutamic acid, Ethanol-water mixed solvent, Self-assembled monolayers, L-cysteine

中图分类号:

O645.5

TrendMD:

周心慧, 王海水. 利用L-半胱氨酸自组装膜和混合溶剂协同作用手性拆分DL-谷氨酸. 高等学校化学学报, 2017, 38(6): 1076.

ZHOU Xinhui, WANG Haishui. Co-effect of L-Cysteine Self-assembled Monolayers and Mixed Solvents on Chiral Separation of DL-glutamic Acid^†. Chem. J. Chinese Universities, 2017, 38(6): 1076.

图/表 7

Fig.1 SEM image(A) and XRD pattern(B) of DL-glutamic acid crystals obtained on chiral L-cysteine SAMs from an aqueous solution

Fig.2 SEM images of glutamic acid crystals obtained on the L-Cys SAMs from the mixed solution of water and ethanol with different volume fractions of ethanolVolume fraction of ethanol: (A) 30%; (B) 40%; (C) 50%; (D) 60%.

Fig.3 Raman spectrum of β-glutamic acid crystal obtained on the L-Cys SAMs from 30% ethanol-water solution

Fig.4 XRD patterns of glutamic acid crystals obtained on L-Cys SAMs from the mixed solution of water and ethanolVolume fraction of ethanol in mixed solution: a. 30%; b. 40%; c. 50%; d. 60%.

Fig.5 HPLC spectrum of glutamic crystals obtained on the SAMs from the 60% ethanol-water mixed solution

Fig.6 HPLC spectrum of glutamic crystals obtained from the 60% ethanol-water mixed solution

Table 1 Chiral separation of racemic glutamic acid

No.	Solvent	Content of D-Glu(%)
No.	Solvent	Solution	Crystals
1	60% ethanol	50	58.25
2	60% ethanol	58.25	66.25
3	60% ethanol	66.25	75.2
4	60% ethanol	75.2	82.2
5	Water	82.2	100

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利用L-半胱氨酸自组装膜和混合溶剂协同作用手性拆分DL-谷氨酸

Co-effect of L-Cysteine Self-assembled Monolayers and Mixed Solvents on Chiral Separation of DL-glutamic Acid^†

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利用L-半胱氨酸自组装膜和混合溶剂协同作用手性拆分DL-谷氨酸

Co-effect of L-Cysteine Self-assembled Monolayers and Mixed Solvents on Chiral Separation of DL-glutamic Acid†

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Co-effect of L-Cysteine Self-assembled Monolayers and Mixed Solvents on Chiral Separation of DL-glutamic Acid^†