Synthesis of Tripeptide Chloromethyl Ketones and Examination of Their Inhibitory Effects on Plasmin and Plasma Kallikrein

Yuko TSUDA; Naoki TENO; Yoshio OKADA; Keiko WANAKA; Miyako BOHGAKI; Akiko HIJIKATA-OKUNOMIYA; Utako OKAMOTO; Taketoshi NAITO; Shosuke OKAMOTO

doi:10.1248/cpb.37.3108

Yuko TSUDA, Naoki TENO, Yoshio OKADA, Keiko WANAKA, Miyako BOHGAKI, Akiko HIJIKATA-OKUNOMIYA, Utako OKAMOTO, Taketoshi NAITO, Shosuke OKAMOTO

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Keywords: synthetic inhibitor, substrate-derived inhibitor, chloromethyl ketone derivative, selective inhibitor, chemical synthesis, plasma kallikrein, plasmin, trypsin-like serine proteinase

JOURNAL FREE ACCESS

1989 Volume 37 Issue 11 Pages 3108-3111

DOI https://doi.org/10.1248/cpb.37.3108

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Abstract

With the aim of obtaining selective synthetic inhibitors of plasmin and plasma kallikrein, D-Ile-Phe-Lys-CH₂Cl, Ile-Phe-Lys-CH₂Cl, D-Ile-Phe-Arg-CH₂Cl and Ile-Phe-Arg-CH₂Cl were synthesized and their inhibitory activity against plasmin, plasma kallikrein and other trypsin-like serine proteinases was examined. Among them, D-Ile-Phe-Arg-CH₂Cl exhibited a highly selective inhibitory activity against plasma kallikrein, yet D-Ile-Phe-Lys-CH₂Cl exhibited nearly the same order of inhibitory activity against plasmin as well as plasma kallikren.

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