Total synthesis of a reported fluorometabolite from Streptomyces sp. TC1 indicates an incorrect assignment. The isolated compound did not contain fluorine

J Nat Prod. 2014 Jun 27;77(6):1249-51. doi: 10.1021/np500260z. Epub 2014 May 21.

Abstract

3,5-Di-tert-butyl-4-fluorophenylpropionic acid (1) was recently reported as a natural product from Streptomyces sp. TC1. This was a notable disclosure because fluorinated natural products are exceedingly rare, and in this case it suggested that the bacterium had the capacity to mediate an enzymatic aryl fluorination reaction. However, a synthesis of the putative metabolite 1 demonstrates that the spectroscopic data are inconsistent with the proposed structure. There is no evidence that the isolated compound contained a fluorine atom.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry*
  • Biological Products / isolation & purification
  • Fluorine / chemistry*
  • Hydrocarbons, Fluorinated / chemistry*
  • Hydrocarbons, Fluorinated / isolation & purification
  • Molecular Structure
  • Streptomyces / chemistry*

Substances

  • Biological Products
  • Hydrocarbons, Fluorinated
  • Fluorine