Synthesis of glutamic acid and glutamine peptides possessing a trifluoromethyl ketone group as SARS-CoV 3CL protease inhibitors |
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| Authors: | Magne O Sydnes Vinay K Sharma Usman Bacha Ernesto Freire |
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| Institution: | a Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Kyoto 607-8412, Japan
b Department of Biology, Johns Hopkins University, Baltimore, MD, USA |
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| Abstract: | Trifluoromethyl-β-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 3CLpro). |
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| Keywords: | Trifluoromethyl ketone Protease inhibitors Severe acute respiratory syndrome coronavirus protease (SARS-CoV 3CLpro) |
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