Journal
TETRAHEDRON
Volume 62, Issue 36, Pages 8601-8609Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.06.052
Keywords
trifluoromethyl ketone; protease inhibitors; severe acute respiratory syndrome coronavirus protease (SARS-CoV 3CL(pro))
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Funding
- NIGMS NIH HHS [R01 GM057144] Funding Source: Medline
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Trifluoromethyl-beta-amino alcohol 11 [(4S)-tert-butyl 4-amino-6,6,6-trifluoro-5-hydroxyhexanoate] was synthesized in five steps starting from Cbz-L-Glu-OH 5 where the key step involved the introduction of the trifluoromethyl (CF3) group to oxazolidinone 7, resulting in the formation of silyl ether 8 [(4S,5S)-benzyl 4-(2-(tert-butoxycarbonyl)ethyl)-5-(trifluoromethyl)-5-(trimethylsilyloxy)oxazolidine-3-carboxylate]. Compound 11 was then converted into four tri- and tetra-glutamic acid and glutamine peptides (1-4) possessing a CF3-ketone group that exhibited inhibitory activity against severe acute respiratory syndrome coronavirus protease (SARS-CoV 3CL(pro)). (c) 2006 Elsevier Ltd. All rights reserved.
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