T. Tamura et al., SYNTHESIS OF FLUOROACETATE FROM FLUORIDE, GLYCEROL, AND BETA-HYDROXYPYRUVATE BY STREPTOMYCES-CATTLEYA, Journal of bacteriology, 177(9), 1995, pp. 2265-2269
Streptomyces cattleya produces fluoroacetate and 4-fluorothreonine fro
m inorganic fluoride added to the culture broth. We have shown by F-19
nuclear magnetic resonance (NMR) spectrometry that fluoroacetate is a
ccumulated first in the culture broth and that accumulation of 4-fluor
othreonine is next. To show precursors of the carbon skeleton of fluor
oacetate, we carried out tracer experiments with various C-14- and C-1
3-labeled compounds. Radioactivity of [U-C-14]glucose, [U-C-14]glycero
l, [U-C-14]serine, and [U-C-14]beta-hydroxypyruvate was incorporated i
nto fluoroacetate to an extent of 0.2 to 0.4%, whereas [3-C-14]pyruvat
e, [2,3-C-14]succinate, and [U-C-14]aspartate were less efficiently in
corporated (0.04 to 0.08%). The addition of [2-C-13]glycerol to the my
celium suspension of Streptomyces cattleya caused exclusive enrichment
of the carboxyl carbon of fluoroacetate with C-13; about 40% of carbo
xyl carbon of fluoroacetate was labeled with C-13. We studied the radi
oactivity incorporation of [3-C-14]-, [U-C-14]-, and [1-C-14]beta-hydr
oxypyruvates to show that C-2 and C-3 of beta-hydroxypyruvate are excl
usively converted to the carbon skeleton of fluoroacetate. These resul
ts suggest that the carbon skeleton of fluoroacetate derives from C-1
and C-2 of glycerol through beta-hydroxypyruvate, whose hydroxyl group
is eventually replaced by fluoride.