Document Detail


Oxidation of aldehydes catalyzed by pig liver flavin-containing monooxygenase.
MedLine Citation:
PMID:  8689949     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Flavin-containing monooxygenase-1 (FMO1) purified to homogeneity from pig liver microsomes catalyzes NADPH- and oxygen-dependent oxidation of salicylaldehyde to pyrocatechol and formate. These products, formed in equimolar amounts, were the only ones detected that suggests that FMO1 catalyzes the oxidation of salicylaldehyde by Baeyer-Villiger chemistry. In addition to salicylaldehyde, 2-hydroxy-1-naphthaldehyde, 5-chlorosalicylaldehyde, 5-nitrosalicylaldehyde, ferrocene carboxaldehyde, 2-pyridine carboxaldehyde, and acetylacetone also stimulated NADPH-dependent oxygen uptake in the presence of FMO1. On the other hand, benzaldehyde, 2-methoxybenzaldehyde, 4-pyridine carboxaldehyde and 3- or 4-hydroxybenzaldehyde, and none of the alkylaldehydes tested had detectable substrate activity. Pig liver FMO1 apparently only catalyzes C-oxidation of reactive aldehydes with a hydrogen ion acceptor function adjacent to the carbonyl.
Authors:
G P Chen; L L Poulsen; D M Ziegler
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Drug metabolism and disposition: the biological fate of chemicals     Volume:  23     ISSN:  0090-9556     ISO Abbreviation:  Drug Metab. Dispos.     Publication Date:  1995 Dec 
Date Detail:
Created Date:  1996-08-29     Completed Date:  1996-08-29     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9421550     Medline TA:  Drug Metab Dispos     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1390-3     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Biochemistry, University of Texas, Austin 78712, USA.
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MeSH Terms
Descriptor/Qualifier:
Aldehydes / metabolism*
Animals
Catalysis
Hydrogen-Ion Concentration
Isoenzymes / metabolism*
Kinetics
Liver / enzymology*
Microsomes, Liver / enzymology
Oxidation-Reduction
Oxygenases / metabolism,  pharmacology*
Swine
Chemical
Reg. No./Substance:
0/Aldehydes; 0/Isoenzymes; 90-02-8/salicylaldehyde; EC 1.13.-/Oxygenases; EC 1.14.13.8/dimethylaniline monooxygenase (N-oxide forming)

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