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Authors: Sagawa T, Togo K, Miyahara C, Ihara H, Ohkubo K
Article Title: Rate-enhancement of hydrolysis of long-chain amino acid ester by cross-linked polymers imprinted with a transition-state analogue: evaluation of imprinting effect in kinetic analysis.
Publication date: 2004
Journal: Analytica Chimica Acta
Volume: 504
Issue: (1)
Page numbers: 37-41.
DOI: 10.1016/S0003-2670(03)00945-0
Alternative URL: http://www.chem.kumamoto-u.ac.jp/~ihara/reprints/aca2004a.pdf
Abstract: Acceleration property of a cross-linked polymer catalyst for the hydrolysis of N-dodecanoyl leucine-p-nitrophenyl ester is attributed to the molecularly imprinting of phenyl- 1- undecylcarbonylamino-3-methylbutyl phosphonate as the template of transition-state analogue (TSA) and 4-[(3'- methacryloylamino)ethyl]imidazole as the binding site of the polymer catalyst. Equimolar complex of the template of the TSA and the binding site of imidazole-containing monomer through the electrostatic interaction and hydrophobic effect: was confirmed by H-1 NMR measurements and the complex was copolymerized with hydrophobic styrene monomer and 10% divinylbenzene cross-linker. A control polymer without the template, but with the cross-linker, was also prepared. After removal of the template, imidazole-containing imprinted polymer gave a ca. two-fold rate-enhancement in comparison to the non- imprinted polymer. (C) 2003 Published by Elsevier B.V
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