Evidence for the formation of Michael adducts from reactions of (E,E)-muconaldehyde with glutathione and other thiols.
Bioorg Chem
; 33(5): 363-73, 2005 Oct.
Article
en En
| MEDLINE
| ID: mdl-16005934
ABSTRACT
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.
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Base de datos:
MEDLINE
Asunto principal:
Compuestos de Sulfhidrilo
/
Aldehídos
/
Glutatión
Idioma:
En
Revista:
Bioorg Chem
Año:
2005
Tipo del documento:
Article
País de afiliación:
Estados Unidos