Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 17, Issue 23, Pages 6563-6566Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2007.09.075
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Funding
- MRC [G0000508, G9722968] Funding Source: UKRI
- Medical Research Council [G9722968, G0000508] Funding Source: researchfish
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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 (CPB2.8 Delta CTE) 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. (c) 2007 Elsevier Ltd. All rights reserved.
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