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Evidence for the formation of Michael adducts from reactions of (E,E)-muconaldehyde with glutathione and other thiols

Lookup NU author(s): Dr Alistair Henderson, Dr Christine Bleasdale, Emeritus Professor Bernard Golding

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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. © 2005 Elsevier Inc. All rights reserved.

Publication metadata

Author(s): Henderson AP, Bleasdale C, Delaney K, Lindstrom AB, Rappaport SM, Waidyanatha S, Watson WP, Golding BT

Publication type: Article

Publication status: Published

Journal: Bioorganic Chemistry

Year: 2005

Volume: 33

Issue: 5

Pages: 363-373

Print publication date: 01/10/2005

ISSN (print): 0045-2068

ISSN (electronic): 1090-2120

Publisher: Elsevier

URL: http://dx.doi.org/10.1016/j.bioorg.2005.05.004

DOI: 10.1016/j.bioorg.2005.05.004

PubMed id: 16005934

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