Synthesis and Properties of Nα-(tert-Butyloxycarbonyl)peptide p-Guanidinophenyl Esters as Trypsin Substrates

Kunihiko ITOH; Haruo SEKIZAKI; Eiko TOYOTA; Kazutaka TANIZAWA

doi:10.1248/cpb.43.2082

Synthesis and Properties of N^α-(tert-Butyloxycarbonyl)peptide p-Guanidinophenyl Esters as Trypsin Substrates

Kunihiko ITOH, Haruo SEKIZAKI, Eiko TOYOTA, Kazutaka TANIZAWA

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Keywords: N^α-(tert-butyloxycarbonyl)peptide p-guanidinophenyl ester, 1-[N, N', -bis(benzyloxycarbonyl)amidino]pyrazole, inverse substrate, trypsin, tryptic hydrolysis, enzyme kinetics

JOURNAL FREE ACCESS

1995 Volume 43 Issue 12 Pages 2082-2087

DOI https://doi.org/10.1248/cpb.43.2082

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Abstract

N^α-(tert-Butyloxycarbonyl)peptide p-guanidinophenyl esters were synthesized by amidination of N^α-(tert-butyloxycarbonyl)peptide p-aminophenyl esters with 1-[N, N'-bis(benzyloxycarbonyl)amidino]pyrazole, followed by deprotection by catalytic hydrogenation, in good total yields. These synthetic esters were characterized as specific substrates for trypsin, and kinetic parameters for the trypsin-catalyzed hydrolysis are presented.

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