Structure of a putative fluorinated natural product from Streptomyces sp. TC1.
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.
Biosystems Chemistry, Department Chemie and Center for Integrated Protein Science Munich (CIPSM), and ‡Department Chemie, Technische Universität München , Lichtenbergstraße 4, 85747 Garching, Germany.
Hülya
H
Aldemir
Stefanie V
SV
Kohlhepp
Tanja
T
Gulder
Tobias A M
TA
Gulder
D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011422:Propionates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*
C000599079:3-(3,5-di-tert-butyl-4-fluorophenyl)propionic acid; D001688:Biological Products; D006845:Hydrocarbons, Fluorinated; D011422:Propionates