Document Detail

Role of tautomerism of 2-azaadenine and 2-azahypoxanthine in substrate recognition by xanthine oxidase.
MedLine Citation:
PMID:  9089433     Owner:  NLM     Status:  MEDLINE    
The tautomerism of 2-azaadenine and 2-hypoxanthine has been examined in the gas phase and in aqueous solution. The tautomerism in the gas phase has been studied by means of semiempirical and ab initio quantum-mechanical computations, as well as density-functional calculations. The influence of the aqueous solvent on the relative stability between tautomers has been estimated from self-consistent reaction field calculations performed with different high-level continuum models. The results provide a detailed picture of the tautomeric preference for these purine bases. The importance of tautomerism in the substrate recognition by xanthine oxidase is discussed. Finally, the rate of oxidation of 2-azaadenine and 2-hypoxanthine by xanthine oxidase is discussed in terms of the recognition model at the enzyme active site.
B Hernández; M Orozco; F J Luque
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of computer-aided molecular design     Volume:  11     ISSN:  0920-654X     ISO Abbreviation:  J. Comput. Aided Mol. Des.     Publication Date:  1997 Mar 
Date Detail:
Created Date:  1997-06-03     Completed Date:  1997-06-03     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  8710425     Medline TA:  J Comput Aided Mol Des     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  153-62     Citation Subset:  IM    
Department of Biochemistry and Molecular Biology, Faculty of Chemistry, University of Barcelona, Spain.
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MeSH Terms
Adenine / analogs & derivatives,  chemistry
Binding Sites
Hypoxanthines / chemistry*
Models, Molecular
Molecular Structure
Substrate Specificity
Xanthine Oxidase / chemistry,  metabolism*
Reg. No./Substance:
0/Gases; 0/Hypoxanthines; 0/Solutions; 2308-56-7/2-azaadenine; 4656-86-4/2-azahypoxanthine; 73-24-5/Adenine; 7732-18-5/Water; EC Oxidase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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