Influence of cross-linking monomer and hydrophobic styrene comonomer on stereoselective esterase activities of polymer catalyst imprinted with a transition-state analogue for hydrolysis of amino acid esters

Abstract Polymer catalysts, cross-linked with N , N ′-ethylene (C 2 ) {or butylene (C 4 )}-bisacrylamide 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}. Maximal stereoselectivity ( l / d =8.4) was obtained by using N , N ′-C 4 -bisacrylamide cross-linked polymer catalyst, which was copolymerized with hydrophobic styrene monomer.