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Dipeptidyl Alpha-Fluorovinyl Michael Acceptors: Synthesis and Activity Against Cysteine Proteases

Koen Steert, Ibrahim El-Sayed, Pieter Van der Veken, Alisa Krishtal, Christian Van Alsenoy, Gareth D Westrop, Jeremy C Mottram, Graham H Coombs, Koen Augustyns, Achiel Haemers

Bioorg Med Chem Lett. 2007 Dec 1;17(23):6563-6.

PMID: 17936625

Abstract:

The synthesis of novel dipeptidyl alpha-fluorovinyl sulfones using a Horner-Wadsworth-Emmons approach on N-Boc-l-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8DeltaCTE) revealed low biological activity. Relative rates of Michael additions of 2'-(phenethyl)thiol with vinyl sulfone and alpha-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing results.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP72155454 N-Boc-L-phenylalaninal N-Boc-L-phenylalaninal 72155-45-4 Price
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