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. 1996 Dec;104(Suppl 6):1201–1209. doi: 10.1289/ehp.961041201

Chemistry of muconaldehydes of possible relevance to the toxicology of benzene.

C Bleasdale 1, G Kennedy 1, J O MacGregor 1, J Nieschalk 1, K Pearce 1, W P Watson 1, B T Golding 1
PMCID: PMC1469744  PMID: 9118894

Abstract

(Z,Z)-Muconaldehyde reacted with primary amines to give N-substituted-2(2'-oxoethyl)-pyrroles, which were reduced to N-substituted-2-(2'-hydroxyethyl)-pyrroles by sodium borohydride. The pyrrole-forming reaction is exhibited by valine and its methyl ester, and is being developed with terminal valine in hemoglobin as a means of dose monitoring (Z,Z)-muconaldehyde, a putative metabolite of benzene. Reactions in aqueous solution between (Z,Z)-muconaldehyde and adenosine, deoxyadenosine, guanosine, or deoxyguanosine leading to pyrrole-containing adducts are described. The elucidation of the structures of the adducts was assisted by the study of reactions between (Z,Z)-muconaldehyde and both nucleoside derivatives and a model compound for guanosine. Reactions of (Z,Z)-muconaldehyde are complicated by its isomerization to (E,Z)- and (E-E)-muconaldehyde. The kinetics of this process have been studied in benzene, acetonitrile, and dimethylsulfoxide.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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