Studies on the reaction of glutathione and formaldehyde using NMR

Org Biomol Chem. 2010 Nov 7;8(21):4915-20. doi: 10.1039/c0ob00208a. Epub 2010 Aug 24.

Abstract

Within cells it is proposed that a major mechanism for the metabolism of formaldehyde is via its reaction with glutathione (GSH) to form S-hydroxymethylglutathione (HMG), which undergoes subsequent oxidation. In addition to HMG and the previously reported (5R,10S)-5-(carboxymethylcarbamoyl)-7-oxo-3-thia-1,6-diazabicyclo[4.4.1]undecane-10-carboxylic acid (BiGF(2)), NMR studies on the reaction of GSH with formaldehyde reveal two previously unassigned monocyclic structures. The results imply that the biologically relevant reactions between aldehydes and peptides/proteins may be more complex than presently perceived.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Formaldehyde / chemistry
  • Formaldehyde / metabolism*
  • Glutathione / chemistry
  • Glutathione / metabolism*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Formaldehyde
  • Glutathione