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Authors: Ohkubo K, Sawakuma K, Sagawa T
Article Title: Shape- and stereo-selective esterase activities of cross-linked polymers imprinted with a transition-state analogue for the hydrolysis of amino acid esters.
Publication date: 2001
Journal: Journal of Molecular Catalysis A: Chemical
Volume: 165
Issue: (1-2)
Page numbers: 1-7.
DOI: 10.1016/S1381-1169(00)00438-6
Abstract: Various cross-linked (with N,N'-ethylene (C-2), butylene (C-4), hexamethylene (C-6) or decamethylene (C-10)-bisacrylamide) polymer catalysts containing L-histidine and quaternary trimethylammonium groups were imprinted with a racemic transition-state analogue of phenyl 1 -benzyloxycarbonyl-3 - methylpentylphosphonate for the hydrolysis of p-nitrophenyl N- (benzyloxycarbonyl)-L (or D)-leucinate (Z-L (or D)-Leu-PNP). Among these polymer catalysts, N,N,N-C-4-bisacrylamide-cross- linked polymer catalyst, which was copolymerized with styrene monomer, exhibited the notable substrate-stereospecificity for the Z-L-Leu-PNP hydrolysis among the hydrolyses of enantiomeric L (or D)-N-protected (such as tert-butyloxycarbonyl (Boc-), acetyl (C-2 -), decanoyl (C-10-) or benzyloxycarbonyl (Z-)) amino acid (Leu, Ala, or Phe) p-nitrophenyl esters in 10 vol.% MeCN-Tris buffer (pH 7.15) at 30 degreesC. (C) 2001 Elsevier Science B.V. All rights reserved
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