Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds

Org Biomol Chem. 2011 May 21;9(10):3920-8. doi: 10.1039/c1ob05131h. Epub 2011 Apr 6.

Abstract

Metabolism of meta-bromobenzoic acid by the blocked mutant Ralstonia eutrophus B9 affords an enantiopure dearomatised halodiene-diol which we demonstrate is a versatile chiron for organic synthesis. The presence of the halogen leads to reactivity that is distinct to that observed for the non-halogenated analogue and also serves as a synthetic handle for further functionalisation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromobenzoates / chemistry*
  • Bromobenzoates / metabolism*
  • Cupriavidus necator / metabolism*
  • Oxidation-Reduction
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Bromobenzoates