Shape- and stereo-selective esterase activities of cross-linked polymers imprinted with a transition-state analogue for the hydrolysis of amino acid esters

Add time:09/26/2019    Source:sciencedirect.com

Various cross-linked (with N,N′-ethylene (C2), butylene (C4), hexamethylene (C6), or decamethylene (C10)-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′-C4-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 (C2-), decanoyl (C10-) or benzyloxycarbonyl (Z-)) amino acid (Leu, Ala, or Phe) p-nitrophenyl esters in 10 vol.% MeCN-Tris buffer (pH 7.15) at 30°C.

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