Formaldehyde metabolism by Escherichia coli. Carbon and solvent deuterium incorporation into glycerol, 1,2-propanediol, and 1,3-propanediol

Biochemistry. 1985 Jul 16;24(15):4148-55. doi: 10.1021/bi00336a050.

Abstract

Escherichia coli were grown on 14.3% uniformly 13C-labeled glucose as the sole carbon source and challenged anaerobically with 90% 13C-labeled formaldehyde. The major multiply labeled metabolites were identified by 13C NMR spectroscopy to be glycerol and 1,2-propanediol, and a minor metabolite was shown to be 1,3-propanediol. In each case, formaldehyde is incorporated only into the C1 position. A novel form of 13C NMR isotope dilution analysis of the major products reveals that all the 1,2-diol C1 is formaldehyde derived but that about 40% of the glycerol C1 is derived from bacterial sources. Glycerokinase converted the metabolite [1-13C]glycerol to equal amounts of [3-13C]glycerol 3-phosphate and [1-13C]glycerol 3-phosphate, demonstrating that the metabolite is racemic. When [13C]formaldehyde incubation was carried out in H2O/D2O mixtures, deuterium incorporation was detected by beta- and gamma-isotope shifts. The 1,3-diol is deuterium labeled only at C2 and only once, while the 1,2-diol and glycerol are each labeled independently at both C2 and C3; C3 is multiply labeled. Deuterium incorporation levels are different for each metabolite, indicating that the biosynthetic pathways probably diverge early.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deuterium
  • Escherichia coli / metabolism*
  • Formaldehyde / metabolism*
  • Glycerol / biosynthesis*
  • Glycerol Kinase / metabolism
  • Magnetic Resonance Spectroscopy
  • Propylene Glycol
  • Propylene Glycols / metabolism*
  • Solvents

Substances

  • Propylene Glycols
  • Solvents
  • Formaldehyde
  • 1,3-propanediol
  • Propylene Glycol
  • Deuterium
  • Glycerol Kinase
  • Glycerol