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Bioorg Med Chem. 2016 Oct 15;24(20):4871-4874. doi: 10.1016/j.bmc.2016.07.012. Epub 2016 Jul 11.

Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

Author information

1
Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107, United States.
2
Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107, United States. Electronic address: scott.miller@yale.edu.

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:

Amino acid; Catalysis; Dioxirane; Oxidation; Peptide

PMID:
27452284
PMCID:
PMC5053897
DOI:
10.1016/j.bmc.2016.07.012
[Indexed for MEDLINE]
Free PMC Article

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