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Reference type: Journal
Authors: Yasuyama T, Matsunaga H, Ando S, Ishizuka T
Article Title: A Study of the Strength of a Template Molecule-A Functional Monomer Interaction That Affects the Performance of Molecularly Imprinted Polymers and Its Application to Chiral Amplification.
Publication date: 2017
Journal: Chemical and Pharmaceutical Bulletin
Volume: 65
Issue: (4)
Page numbers: 396-402.
DOI: 10.1248/cpb.c16-00974
Alternative URL: https://www.jstage.jst.go.jp/article/cpb/65/4/65_c16-00974/_article

Abstract: A novel type of molecularly imprinted polymer (MIP), N-benzoyl-(S)-valine anilide-imprinted polymer (IP-2), was prepared using hydrogen-bonding interactions as a main force in the pre-polymerization step. The performance of the IP-2 was evaluated via batch procedure and compared with a (S)-valine anilide-imprinted polymer (IP-1) that was prepared using an ionic interaction that is stronger than hydrogen bonding. Although both polymers showed a preferential adsorbability for (S)-amino acid derivatives, different performances were observed in terms of adsorbability and enantioselectivity. In addition, the IP-2 was able to recognize the enantiomer of a valine-derived chiral catalyst. This phenomenon was applied to a chiral amplification reaction, and a highly selective asymmetric Mannich-type amination was achieved using the combination of a racemic catalyst and a MIP
Template and target information: N-benzoyl-(S)-valine anilide, (S)-valine anilide
Author keywords: molecularly imprinted polymer, chiral recognition, (S)-benzoyl amino acid anilide, asymmetric amplification


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