Total Synthesis of a Reported Fluorometabolite from Streptomyces sp TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

Mohammed Salah Ayoup, David B. Cordes, Alexandra M. Z. Slawin, David O'Hagan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1249-1251
Number of pages3
JournalJournal of Natural Products
Volume77
Issue number6
DOIs
Publication statusPublished - Jun 2014

Keywords

  • ANTIOXIDANTS
  • ACCEPTOR
  • POTENT

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