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

doi:10.7503/cjcu20160866

Abstract

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

CLC Number:

O645.5

TrendMD:

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

Figures/Tables 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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