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

نویسندگان

  • C Bleasdale
  • G Kennedy
  • J O MacGregor
  • J Nieschalk
  • K Pearce
  • W P Watson
  • B T Golding
چکیده

(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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عنوان ژورنال:
  • Environmental Health Perspectives

دوره 104  شماره 

صفحات  -

تاریخ انتشار 1996