Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

Org Biomol Chem. 2017 Oct 4;15(38):8006-8008. doi: 10.1039/c7ob02163a.

Abstract

Deuterium incorporations from [2H1]-(1R,2R) and [2H1]-(1S,2R) glycerols into the fluorine containing antibiotic nucleocidin, in Streptomyces calvus indicate that one deuterium atom is incorporated at the C-5' site of nucleocidin from each of these isotopomers of glycerol. Two deuteriums become incorporated at C-5' of nucleocidin after a feeding experiment with [2H5]-glycerol. These observations indicate that there is no obligate oxidation of the pro-R hydroxymethyl group of glycerol as it progresses through the pentose phosphate pathway and becomes incorporated into the fluorinated antibiotic.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / biosynthesis
  • Adenosine / chemistry
  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemistry
  • Glycerol / analogs & derivatives*
  • Glycerol / chemistry*
  • Molecular Structure
  • Streptomyces / metabolism*

Substances

  • Anti-Bacterial Agents
  • nucleocidin
  • Adenosine
  • Glycerol