Document Detail


Oxidation of 5-hydroxy-2'-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products.
MedLine Citation:
PMID:  15161271     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Oxidation products of cytosine, including 5-hydroxycytosine and 5-hydroxyuracil, are highly susceptible to subsequent oxidation. Here, the oxidation products of 5-hydroxy-2'-deoxyuridine have been studied by NMR and MS analyses. The initial products were diastereomers of isodialuric acid nucleoside. These products subsequently decomposed into corresponding dialuric acid derivatives at neutral pH. The position of the carbonyl and hydroxyl groups, at C5 and C6 for isodialuric acid and at C6 and C5 for dialuric acid derivatives, respectively, was determined by 1H- and 13C NMR analyses. In addition, these analyses revealed that the carbonyl groups of both isodaluric and dialuric acid derivatives exist in their fully hydrated form in aqueous solution. Finally, the dialuric acid derivatives were observed to undergo subsequent decomposition into the corresponding 5-hydroxyhydantoin derivatives. Studies of a trinucleotide containing 5-hydroxyuracil suggest that the reactions described herein for the monomer can be extrapolated to DNA.
Authors:
Johann Rivière; François Bergeron; Sébastien Tremblay; Didier Gasparutto; Jean Cadet; J Richard Wagner
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  126     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2004 Jun 
Date Detail:
Created Date:  2004-05-26     Completed Date:  2004-11-04     Revised Date:  2008-01-17    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6548-9     Citation Subset:  IM    
Affiliation:
Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Sherbrooke, Quebec J1H 5N4, Canada.
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MeSH Terms
Descriptor/Qualifier:
Barbiturates / chemical synthesis*,  chemistry
Deoxyuridine / analogs & derivatives*,  chemistry*
Hydantoins / chemical synthesis*,  chemistry
Molecular Structure
Oxidation-Reduction
Uracil / analogs & derivatives*,  chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Barbiturates; 0/Hydantoins; 102636-37-3/isodialuric acid; 444-15-5/dialuric acid; 5168-36-5/5-hydroxy-2'-deoxyuridine; 66-22-8/Uracil; 951-78-0/Deoxyuridine

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


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