✦ LIBER ✦

Synthesis of peptide fluoromethyl ketones and the inhibition of human cathepsin B

✍ Scribed by David Rasnick

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 432 KB
Volume: 149
Category: Article
ISSN: 0003-2697
DOI: 10.1016/0003-2697(85)90598-6

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✦ Synopsis

Peptide fluoromethyl ketones have been synthesized for the first time. The inhibitor 3-(Nbenzyloxycarbonylphenylalanylamido)-DL-l-fluoro-2-butanone (Z-Phe-AlaCHZF) was found to be a 30-fold more potent inactivator of human cathepsin B than 3-(N-benzyloxycarbonylphenylalanylamido)~L-I-diazo-2-butanone (Z-Phe-AlaCHN& but less reactive than 3-(N-benzyloxycarbonylphenylalanylamido)-~-l-chloro-2-butanone (Z-Phe-AlaCH,Cl). The fluoromethyl ketone's increased potency over the diazomethyl ketone is mainly due to its tighter binding to cathepsin B, with little difference between their respective 5 values. Both Z-Phe-AlaCHN* and Z-Phe-AlaCH*F were quite stable to high concentrations of dithiothreitol, while Z-Phe-AlaCH,Cl was rapidly destroyed by the thiol. 0 1985 Academic press. hc.

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