Efficient synthesis of suitably protected β-difluoroalanine and γ-difluorothreonine from L-ascorbic acid

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) Fluorinated amino acids are useful building blocks for the preparation of biologically active peptides and peptidomimetics with increased metabolic stability. We report here the synthesis of two fluorinated amino acids, β-difluoroalanine and γ-difluorothreonine, as analogues of Ser and Thr, respectively. These compounds were suitably protected for Fmoc-based solid-phase peptide synthesis. Once incorporated into peptides, they may serve as alternative substrates or inhibitors of lantibiotic synthetases that posttranslationally dehydrate Ser and Thr residues to dehydroalanine and dehydrobutyrine, respectively.

Original languageEnglish (US)
Pages (from-to)41-44
Number of pages4
JournalOrganic Letters
Volume9
Issue number1
DOIs
StatePublished - Jan 4 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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