title: Chemistry of muconaldehydes of possible relevance to the toxicology of benzene.
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.
authors.affiliation: Department of Chemistry, University of Newcastle upon Tyne, United Kingdom.
authors.forename: C
authors.initials: C
authors.lastname: Bleasdale
authors.forename: G
authors.initials: G
authors.lastname: Kennedy
authors.forename: J O
authors.initials: JO
authors.lastname: MacGregor
authors.forename: J
authors.initials: J
authors.lastname: Nieschalk
authors.forename: K
authors.initials: K
authors.lastname: Pearce
authors.forename: W P
authors.initials: WP
authors.lastname: Watson
authors.forename: B T
authors.initials: BT
authors.lastname: Golding
mesh_terms: D000447:Aldehydes / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity*; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry / Q000187:drug effects; D000818:Animals; D001554:Benzene / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity*; D002417:Cattle; D004247:DNA / Q000737:chemistry / Q000187:drug effects; D018736:DNA Adducts / Q000737:chemistry; D006801:Humans; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D010455:Peptides / Q000737:chemistry / Q000187:drug effects
chemical_list: D000447:Aldehydes; D000588:Amines; D000596:Amino Acids; D018736:DNA Adducts; D009705:Nucleosides; D010455:Peptides; C034476:muconaldehyde; D004247:DNA; D001554:Benzene