title: Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.
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.
authors.affiliation: Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107, United States.
authors.forename: Aaron L
authors.initials: AL
authors.lastname: Featherston
authors.affiliation: Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107, United States. Electronic address: scott.miller@yale.edu.
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D010649:Phenylalanine / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004852:Epoxy Compounds; D007659:Ketones; D010455:Peptides; C061799:dioxirane; D010649:Phenylalanine
keywords: Amino acid; Catalysis; Dioxirane; Oxidation; Peptide