Work

Efficient Synthesis of Suitably Protected β-Difluoroalanine and γ-Difluorothreonine from l -Ascorbic Acid

Year: 2006

Type: article

Abstract: [reaction: see text] 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, beta-difluoroalanine and gamma-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.

Source: Organic Letters

DOI: 10.1021/ol062401a

Authors: Gongyong Li, Wilfred A. van der Donk

Institution: University of Illinois Urbana-Champaign

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences, National Center for Research Resources

Awards: G5797569311, Posttranslational Modifications in Natural Product Biosynthesis, CONSOLE REPLACEMENT FOR GN500 FTNMR SPECTROMETER