Jtg. Hamilton et al., EXPLORING THE BIOSYNTHETIC ORIGIN OF FLUOROACETATE AND 4-FLUOROTHREONINE IN STREPTOMYCES-CATTLEYA, Journal of the Chemical Society. Perkin transactions. I, (4), 1998, pp. 759-767
The biosynthesis of the fluorometabolites, fluoroacetate and 4-fluorot
hreonine, has been investigated in cell suspensions of Streptomyces ca
ttleya using both carbon-13 and deuterium labelled precursors, The ext
ent of incorporation of label into each metabolite and the distributio
n of label within each metabolite has been determined by GC-MS and F-1
9{H-1} 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 p
hosphate, from which the substrate for fluorination is derived. The st
riking similarity between the labelling patterns within the two fluoro
metabolites recorded in every experiment demonstrates that there is a
single fluorination enzyme in S. cattleya.