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Reference type: Journal
Authors: Xiao XD, Li ZQ, Liu Y, Jia L
Article Title: Preparation of chitosan-based molecularly imprinted material for enantioseparation of racemic mandelic acid in aqueous medium by solid phase extraction.
Publication date: 2019
Journal: Journal of Separation Science
Volume: 42
Issue: (23)
Page numbers: 3544-3552.
DOI: 10.1002/jssc.201900825

Abstract: An S-mandelic acid imprinted chitosan resin was synthesized by cross-linking chitosan with glutaraldehyde in 2% acetic acid solution. S-Mandelic acid imprinted chitosan resin was used to enantioselectively separate racemic mandelic acid in aqueous medium. When keeping the pH of sample solution (100 mM Tris-H3PO4) at 3.5 and adsorption time at 40 min, the enantiomer excess of mandelic acid in supernatant was 78.8%. The adsorption capacities of S-mandelic acid imprinted chitosan resin for S- and R-mandelic acid were determined to be 29.5 and 2.03 mg/g, respectively. While the adsorption capacities of non-imprinted cross-linked chitosan for S- and R-mandelic acid were 2.10 and 2.08 mg/g, respectively. The result suggests that the imprinted caves in S-mandelic acid imprinted chitosan resin are highly matched with S-mandelic acid molecule in space structure and spatial arrangement of action sites. Interestingly, the enantiomer excess value of mandelic acid in supernatant after adsorption of racemic mandelic acid by R-mandelic acid imprinted cross-linked chitosan was 25.4%. The higher enantiomer excess value by S-mandelic acid imprinted chitosan resin suggests that the chiral carbons in chitosan and the imprinted caves in S-mandelic acid imprinted chitosan resin combine to play roles for the enantioselectivity of S-mandelic acid imprinted chitosan resin toward S-mandelic acid. Furthermore, the excellent enantioselectivity of S-mandelic acid imprinted chitosan resin toward S-mandelic acid demonstrates that using chiral chitosan as functional monomer to prepare molecularly imprinted polymers has great potential in enantioseparation of chiral pharmaceuticals
Template and target information: mandelic acid
Author keywords: chiral separation, chitosan, mandelic acid, Molecularly imprinted polymers, solid phase extraction


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