SYNTHESIS OF FLUOROACETATE FROM FLUORIDE, GLYCEROL, AND BETA-HYDROXYPYRUVATE BY STREPTOMYCES-CATTLEYA

Citation
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
Citations number
19
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Microbiology
Journal title
ISSN journal
0021-9193
Volume
177
Issue
9
Year of publication
1995
Pages
2265 - 2269
Database
ISI
SICI code
0021-9193(1995)177:9<2265:SOFFFG>2.0.ZU;2-4
Abstract
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.