Document Detail

In vitro Dimroth rearrangement of 1-(2-carboxyethyl) adenine to N6-(2-carboxyethyl)adenine in single-stranded calf thymus DNA.
MedLine Citation:
PMID:  45009     Owner:  NLM     Status:  MEDLINE    
The new adduct N6-(2-carboxyethyl)adenine (N6-CEA) was prepared from 1-(2-carboxyethyl)adenine (1-CEA) by base catalyzed (Dimroth) rearrangement of 1-CEA. The structure of N6-CEA was assigned on the basis of UV spectra and electron impact and isobutane chemical ionization mass spectra. When the carcinogen beta-propiolactone was reacted in vitro with calf thymus DNA, 1-CEA but not N6-CEA was detected on paper chromatograms following acid hydrolysis of the DNA. When BPL-reacted single-stranded DNA was incubated at pH 11.7 (37 degrees C, 18 h) prior to acid hydrolysis, it was found that 1-CEA was completely converted to N6-CEA in DNA by Dimroth rearrangement, whereas no conversion occurred at pH 7.5. The extent of Dimroth rearrangement at various pHs and temperatures was determined for 1-CEA, 1-methyladenine (1-MeA), 1-(2-carboxyethyl)-deoxyadenosine-5'-monophosphoric acid (1-CEdAdo5'P) and the phosphodiester 5'-O-(2-carboxyethyl)phosphono-1-(2-carboxyethyl)deoxyadenosine (1-CE-Ado-5'-P-CE).
A Segal; U Maté; J J Solomon
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Chemico-biological interactions     Volume:  28     ISSN:  0009-2797     ISO Abbreviation:  Chem. Biol. Interact.     Publication Date:  1979 Dec 
Date Detail:
Created Date:  1980-10-24     Completed Date:  1980-10-24     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0227276     Medline TA:  Chem Biol Interact     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  333-44     Citation Subset:  IM    
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MeSH Terms
Adenine / analogs & derivatives*,  isolation & purification,  metabolism
Chemical Phenomena
DNA, Single-Stranded*
Deoxyadenine Nucleotides / metabolism
Hot Temperature
Hydrogen-Ion Concentration
Nucleic Acid Conformation
Thymus Gland
Time Factors
Reg. No./Substance:
0/5'-O-(2-carboxyethyl)phosphono-1-(2-carboxyethyl)deoxyadenosine; 0/DNA, Single-Stranded; 0/Deoxyadenine Nucleotides; 0/Lactones; 5142-22-3/1-methyladenine; 57-57-8/Propiolactone; 64920-12-3/1-(2-carboxyethyl)adenine; 73-24-5/Adenine; 73094-99-2/N(6)-(2-carboxyethyl)adenine; 73095-00-8/1-(2-carboxyethyl)deoxyadenosine 5'-monophosphate

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

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