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

✍ Scribed by Katsutoshi Ohkubo; Kohei Sawakuma; Takashi Sagawa

• Book ID: 104421226
• Publisher: Elsevier Science
• Year: 2001
• Tongue: English
• Weight: 244 KB
• Volume: 165
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/s1381-1169(00)00438-6

✦ Synopsis

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 transitionstate 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 -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 • C.