869731-10-2Relevant academic research and scientific papers
Evidence for the formation of Michael adducts from reactions of (E,E)-muconaldehyde with glutathione and other thiols
Henderson, Alistair P.,Bleasdale, Christine,Delaney, Kirsty,Lindstrom, Andrew B.,Rappaport, Stephen M.,Waidyanatha, Suramya,Watson, William P.,Golding, Bernard T.
, p. 363 - 373 (2005)
Glutathione induces the rapid isomerization of (Z,Z)-muconaldehyde to (E,E)-muconaldehyde via (E,Z)-muconaldehyde, probably via reversible Michael addition of the thiol to one of the enal moieties of the muconaldehyde. Reactions of (E,E)-muconaldehyde with glutathione (in the presence and absence of equine glutathione S-transferase), phenylmethanethiol, N-acetyl-l-cysteine, and N-acetyl-l-cysteine methyl ester were investigated using mass spectrometric techniques. In each case, evidence was obtained for the formation of Michael adducts, e.g., reaction between (E,E)-muconaldehyde and glutathione gave 4-glutathionyl-hex-2-enedial and 3,4-bis-glutathionyl-hexanedial. These experiments suggest that (Z,Z)-muconaldehyde, a putative metabolite of benzene, could lead to the long established urinary metabolite of benzene, (E,E)-muconic acid, via glutathione-mediated isomerization to (E,E)-muconaldehyde.
