Jump to main content
Jump to site search

Issue 20, 2007
Previous Article Next Article

Glutathione traps formaldehyde by formation of a bicyclo[4.4.1]undecane adduct

Author affiliations

Abstract

Glutathione forms complex reaction products with formaldehyde, which can be further modified through enzymatic modification. We studied the non-enzymatic reaction between glutathione and formaldehyde and identified a bicyclic complex containing two equivalents of formaldehyde and one glutathione molecule by protein X-ray crystallography (PDB accession number 2PFG). We have also used 1H, 13C and 2D NMR spectroscopy to confirm the structure of this unusual adduct. The key feature of this adduct is the involvement of the γ-glutamyl α-amine and the Cys thiol in the formation of the bicyclic ring structure. These findings suggest that the structure of GSH allows for bi-dentate masking of the reactivity of formaldehyde. As this species predominates at near physiological pH values, we suggest this adduct may have biological significance.

Graphical abstract: Glutathione traps formaldehyde by formation of a bicyclo[4.4.1]undecane adduct

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 May 2007, accepted on 16 Aug 2007 and first published on 29 Aug 2007


Article type: Paper
DOI: 10.1039/B707602A
Org. Biomol. Chem., 2007,5, 3363-3367

  •   Request permissions

    Glutathione traps formaldehyde by formation of a bicyclo[4.4.1]undecane adduct

    R. Bateman, D. Rauh and K. M. Shokat, Org. Biomol. Chem., 2007, 5, 3363
    DOI: 10.1039/B707602A

Search articles by author

Spotlight

Advertisements