title: Bioorganotin chemistry: a commentary on the reactions of organotin compounds with a cytochrome P-450 dependent monooxygenase enzyme system.
abstract: The biological oxidation of several tributyltin derivatives, by a cytochrome P-450 dependent monooxygenase enzyme system with reduced nicotinamideadeninedinucleotidephosphate as the essential cofactor, produced carbon-hydroxylated compounds identified as alpha-, beta-, gamma- and delta-hydroxybutyldibutyltin derivatives. The hydroxylation pattern and the lack of oxidative cleavage of tin-carbon bonds strongly suggest a free radical rather than an oxenoid mechanism, while the predominance of beta-carbon-hydroxylation further implies some role of the tin-carbon sigma electrons in directing the site of hydroxylation.
mesh_terms: D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003577:Cytochrome P-450 Enzyme System / Q000494:pharmacology*; D008862:Microsomes, Liver / Q000378:metabolism*; D009947:Organotin Compounds / Q000378:metabolism*; D010105:Oxygenases / Q000378:metabolism*; D051381:Rats; D014220:Trialkyltin Compounds / Q000378:metabolism
chemical_list: D009947:Organotin Compounds; D014220:Trialkyltin Compounds; C011559:tributyltin; D003577:Cytochrome P-450 Enzyme System; D010105:Oxygenases