Azapeptides as inhibitors and active site titrants for cysteine proteinases

R Xing, RP Hanzlik

Index: Xing, Ruye; Hanzlik, Robert P. Journal of Medicinal Chemistry, 1998 , vol. 41, # 8 p. 1344 - 1351

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Citation Number: 61

Abstract

Ester and amide derivatives of α-azaglycine (carbazic acid, H2NNHCOOH), α-azaalanine, and α-azaphenylalanine (ie, Ac-l-Phe-NHN (R) CO-X, where X= H, CH3, or CH2Ph, respectively) were synthesized and evaluated as inhibitors of the cysteine proteinases papain and cathepsin B. The ester derivatives inactivated papain and cathepsin B at rates which increased dramatically with leaving group hydrophobicity and electronegativity. For ...