In vitro Dimroth rearrangement of 1-(2-carboxyethyl) adenine to N6-(2-carboxyethyl)adenine in single-stranded calf thymus DNA

Chemico-biological Interactions
A SegalJ J Solomon

Abstract

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).

References

Jan 1, 1975·The International Journal of the Addictions·J G BruhnH D Gouin
Jan 1, 1972·Annual Review of Biochemistry·M MeselsonJ Heywood
Oct 1, 1968·Biochemistry·J B Macon, R Wolfenden
Oct 1, 1963·The Biochemical Journal·P D LAWLEY, P BROOKES

Related Concepts

1-methyladenine
N(6)-(2-carboxyethyl)adenine
1-(2-carboxyethyl)adenine
1-(2-carboxyethyl)deoxyadenosine 5'-monophosphate
5'-O-(2-carboxyethyl)phosphono-1-(2-carboxyethyl)deoxyadenosine
Adenine
Metazoa
Bos indicus
Deoxyadenine Nucleotides
DNA, Single-Stranded

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