Total synthesis of a reported fluorometabolite from Streptomyces sp. TC1 indicates an incorrect assignment. The isolated compound did not contain fluorine.
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.
School of Chemistry, University of St Andrews , North Haugh, St Andrews, KY16 9ST, U.K.
Mohammed Salah
MS
Ayoup
David B
DB
Cordes
Alexandra M Z
AM
Slawin
David
D
O'Hagan
D001688:Biological Products / Q000737:chemistry* / Q000302:isolation & purification; D005461:Fluorine / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry*
D001688:Biological Products; D006845:Hydrocarbons, Fluorinated; D005461:Fluorine