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

doi:10.7503/cjcu20160460

Abstract

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:

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^†[J]. Chem. J. Chinese Universities, 2016, 37(11): 1960.

Figures/Tables 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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