| In vitro Dimroth rearrangement of 1-(2-carboxyethyl) adenine to N6-(2-carboxyethyl)adenine in single-stranded calf thymus DNA. | |
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MedLine Citation:
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PMID: 45009 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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). |
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Authors:
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A Segal; U Maté; J J Solomon |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Chemico-biological interactions Volume: 28 ISSN: 0009-2797 ISO Abbreviation: Chem. Biol. Interact. Publication Date: 1979 Dec |
Date Detail:
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Created Date: 1980-10-24 Completed Date: 1980-10-24 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0227276 Medline TA: Chem Biol Interact Country: NETHERLANDS |
Other Details:
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Languages: eng Pagination: 333-44 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Adenine
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analogs & derivatives*,
isolation & purification,
metabolism Animals Cattle Chemical Phenomena Chemistry DNA, Single-Stranded* Deoxyadenine Nucleotides / metabolism Hot Temperature Hydrogen-Ion Concentration Lactones* Nucleic Acid Conformation Propiolactone* Thymus Gland Time Factors |
| Chemical | |
Reg. No./Substance:
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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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