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

Polymer catalysts, cross-linked with N,N′-ethylene (C2) {or butylene (C4)}-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′-C4-bisacrylamide cross-linked polymer catalyst, which was copolymerized with hydrophobic styrene monomer.