Document Detail

Systematic study on the mechanism of aldehyde oxidation to carboxylic acid by cytochrome P450.
MedLine Citation:
PMID:  17661096     Owner:  NLM     Status:  MEDLINE    
The mechanism of aldehyde to carboxylic acid conversion catalyzed by P450 enzymes via a series of reactions was studied systematically for the first time with density functional theory calculations. A two-state reactivity mechanism has been proposed, which can be adopted for many aldehyde oxidation reactions catalyzed by P450 enzymes. The mechanism involves initial hydrogen abstraction as the rate-limiting step and this is followed by steps of oxygen rebound without barriers owing to the quick recombination of the resultant radical species. Meanwhile, in an attempt to explore whether there exist some rules for the hydroxylation of aldehyde substrates by P450, the transition state barriers of the rate-limiting step for a series of aldehyde hydroxylation reactions have been compared. A predictive pattern of extended barrier/bond energy correlation for different hydroxylations of aldehyde substrates by P450 has been established, which was further confirmed to be a reliable reactivity scale by experimental results.
Xiaojing Liu; Yong Wang; Keli Han
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Publication Detail:
Type:  Journal Article     Date:  2007-07-28
Journal Detail:
Title:  Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry     Volume:  12     ISSN:  0949-8257     ISO Abbreviation:  J. Biol. Inorg. Chem.     Publication Date:  2007 Sep 
Date Detail:
Created Date:  2007-09-03     Completed Date:  2007-12-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9616326     Medline TA:  J Biol Inorg Chem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1073-81     Citation Subset:  IM    
State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, People's Republic of China.
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MeSH Terms
Aldehydes / chemistry*
Carboxylic Acids / chemistry*
Computer Simulation*
Cytochrome P-450 Enzyme System / chemistry*
Formaldehyde / chemistry
Models, Chemical
Molecular Structure
Structure-Activity Relationship
Reg. No./Substance:
0/Aldehydes; 0/Carboxylic Acids; 50-00-0/Formaldehyde; 9035-51-2/Cytochrome P-450 Enzyme System

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