Facile chemoselective synthesis of dehydroalanine-containing peptides

Nicole M. Okeley, Yantao Zhu, Wilfred A. Van Der Donk

Research output: Contribution to journalArticlepeer-review

Abstract

(matrix presented) Useful methodology is described for the synthesis of dehydroalanine residues (II) within peptides. The unnatural amino acid (Se)-phenylselenocysteine (I) can be incorporated into growing peptide chains via standard peptide synthesis procedures. Subsequent oxidative elimination affords a dehydroalanine at the desired position. The oxidation conditions are mild and tolerate functionalities commonly found in peptides, including variously protected cysteine residues. To illustrate its utility, cyclic lanthionines have been synthesized by this method.

Original languageEnglish (US)
Pages (from-to)3603-3606
Number of pages4
JournalOrganic Letters
Volume2
Issue number23
DOIs
StatePublished - Nov 16 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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