Studies on the cytochrome P450 catalyzed oxidation of 13C labeled 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine by 13C NMR.
Bioorg Med Chem
; 13(8): 2975-80, 2005 Apr 15.
Article
em En
| MEDLINE
| ID: mdl-15781407
ABSTRACT
A recent study from Hanzlik's laboratory (J. Am. Chem. Soc. 2002, 124, 8268) has provided compelling evidence of a hydrogen atom transfer pathway for the cytochrome P450-catalyzed oxidative N-decyclopropylation of N-cyclopropyl-N-methylaniline. In the present paper, we report an analogous pathway for the oxidative decyclopropylation of a 13C-labeled 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridinyl substrate. Three 13C-enriched metabolites were characterized (1) a diastereomeric pair of N-cyclopropyl-N-oxides; (2) the N-cyclopropylpyridinium species; and (3) cyclopropanone hydrate. These results extend the hydrogen atom transfer pathway to include aliphatic tertiary amine substrates. Consideration of all of the available evidence, however, leads us to conclude that the cytochrome P450-catalyzed alpha-carbon oxidations of cyclopropylamines may proceed via both the single electron and hydrogen atom transfer pathways.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Piridinas
/
Sistema Enzimático do Citocromo P-450
Idioma:
En
Revista:
Bioorg Med Chem
Ano de publicação:
2005
Tipo de documento:
Article