Structure of a putative fluorinated natural product from Streptomyces sp. TC1.

J Nat Prod

Biosystems Chemistry, Department Chemie and Center for Integrated Protein Science Munich (CIPSM), and ‡Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany.

Published: November 2014

AI Article Synopsis

  • Fluorine-containing natural products are very rare, making the discovery of 3-(3,5-di-tert-butyl-4-fluorophenyl)propionic acid notable as it features the first known aromatic fluorine in any natural product.
  • The discovery raised hopes of identifying an enzyme responsible for aromatic fluorination in the bacteria Streptomyces sp. TC1.
  • Upon reviewing the initial analytical data for this compound, inconsistencies were found, leading to further investigation to validate the reported structure.

Article Abstract

Fluorine-containing natural products are extremely rare. The recent report on the isolation and biological activity of the bacterial secondary metabolite 3-(3,5-di-tert-butyl-4-fluorophenyl)propionic acid was thus highly remarkable. The compound contained the first aromatic fluorine substituent known to date in any natural product. The promise to discover an enzyme capable of aromatic fluorination in the producing strain Streptomyces sp. TC1 prompted our immediate interest. A close inspection of the originally reported analytical data of the fluoro metabolite revealed inconsistencies that triggered us to validate the reported structure. The results of these efforts are presented in this communication.

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Source
http://dx.doi.org/10.1021/np500643gDOI Listing

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