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Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis
Affiliation:1. Unité Mixte de Recherche No. 7565, Université de Lorraine, B.P. 70239, 54506 Vandoeuvre-lès-Nancy cedex, France;2. Laboratoire International Associé Centre National de la Recherche Scientifique et University of Illinois at Urbana–Champaign, CNRS, B.P. 70239, 54506 Vandoeuvre-lès-Nancy cedex, France;3. Department of Physics, University of Illinois at Urbana−Champaign, 1110 West Green Street, Urbana, IL 61801, USA;4. Bases Moléculaires et Structurales des Systèmes Infectieux, IBCP, UMR 5086, Université de Lyon, 69367 Lyon, France;5. Bases Moléculaires et Structurales des Systèmes Infectieux, IBCP, UMR 5086, CNRS, 69367 Lyon, France;1. Department of Chemistry, Johns Hopkins University, 3400 N. Charles St., Baltimore, MD 21218, USA;2. Department of Chemistry, Sonoma State University, 1801 E. Cotati Ave., Rohnert Park, CA 94928, USA;1. School of Functional Food and Wine, Shenyang Pharmaceutical University, Shenyang 110016, China;2. Key Laboratory of Structure-based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China
Abstract:We report the synthesis of phenylalanine-derived trifluoromethyl ketones for the in situ generation of dioxiranes for the purpose of oxidation catalysis. The key features of this synthesis include the use of a masked ketone strategy and a Negishi cross-coupling to access the parent amino acid. The derivatives can be readily incorporated into a peptide for use in oxidation chemistry and exhibit good stability and reactivity.
Keywords:Peptide  Catalysis  Oxidation  Dioxirane  Amino acid
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