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Reference type: Journal
Authors: Ohkubo K, Funakoshi Y, Urata Y, Hirota S, Usui S, Sagawa T, Yoshinaga K
Article Title: Molecular design of transition-state analog-imprinted polymer catalysts-stereoselective esterolysis of amino-acid esters.
Publication date: 1995
Journal: Kobunshi Ronbunshu
Volume: 52
Issue: (10)
Page numbers: 644-649.
DOI: 10.1295/koron.52.644

Abstract: Molecular design of polymer catalysts for the esterolysis of a marked amino acid ester substrate Z-L-Leu-PNP (PNP=p-nitrophenol) was performed. Either a transition-state analogue of Z-Leu-PP (phenyl 1- benzyloxycarbonly-3-methylpentylphosphonate) or a ground-state analogue of Z-L-Leu-AA (ethyl N-benzyloxycarbonyl-L-leucine- anthranilate) was used as a template molecule. In the esterolyses of amino acid esters in 10 vol% dimethyl sulfoxide (DMSO)-Tris buffer (pH 7.15) at 293 similar to 308 K, several water-soluble or insoluble polymer catalysts containing a L-histidine catalytic site, which were synthesized by the radical polymerization with acrylamide derivatives, incorporated the marked substrate into their reaction cavities effectively. An ammonium-chain containing water-soluble polymer catalyst exhibited a remarkable acceleration of the present reaction. The free energy of activation (23.9 kcal/mol at 303 K) of the uncatalyzed reaction decreased 7.0 kcal/mol
Template and target information: Z-Leu-PP, phenyl 1-benzyloxycarbonly-3-methylpentylphosphonate, Z-L-Leu-AA, ethyl N-benzyloxycarbonyl-L-leucine-anthranilate, Z-L-Leu-PNP (PNP=p-nitrophenol)

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