Total Synthesis and Stereochemistry Assignment of Nucleoside Antibiotic A-94964

Angew Chem Int Ed Engl. 2022 Mar 28;61(14):e202200818. doi: 10.1002/anie.202200818. Epub 2022 Feb 16.

Abstract

A collective total synthesis of eight diastereoisomers associated with NMR analysis leads to a full stereochemistry assignment of the structurally unique nucleoside antibiotic A-94964, which features an octuronic acid uridine core decorated with an α-D-mannopyranosyl residue and an α-D-N-acylglucosaminopyranosyl residue via a phosphodiester bridge.

Keywords: A-94964; Nucleoside Antibiotic; Octuronic Acid Uridine; Phosphodiester; Total Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Disaccharides
  • Magnetic Resonance Spectroscopy
  • Nucleosides* / chemistry
  • Pyrimidine Nucleotides
  • Stereoisomerism

Substances

  • A 94964
  • Anti-Bacterial Agents
  • Disaccharides
  • Nucleosides
  • Pyrimidine Nucleotides