Exploring the biosynthetic origin of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya

Abstract

The biosynthesis of the fluorometabolites, fluoroacetate and 4-fluorothreonine, has been investigated in cell suspensions of Streptomyces cattleya using both carbon-13 and deuterium labelled precursors. The extent of incorporation of label into each metabolite and the distribution of label within each metabolite has been determined by GC–MS and ¹⁹F{¹H} NMR spectral analyses. Efficient metabolism of glycine, serine and pyruvate into the fluorometabolites is observed, the results being consistent with metabolism via oxaloacetate to an intermediate in the glycolytic pathway between phosphoenolpyruvate and dihydroxyacetone phosphate, from which the substrate for fluorination is derived. The striking similarity between the labelling patterns within the two fluorometabolites recorded in every experiment demonstrates that there is a single fluorination enzyme in S. cattleya.