In vitro Dimroth rearrangement of 1-(2-carboxyethyl) adenine to N6-(2-carboxyethyl)adenine in single-stranded calf thymus DNA.
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).
D000225:Adenine / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism; D000818:Animals; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D004277:DNA, Single-Stranded; D003838:Deoxyadenine Nucleotides / Q000378:metabolism; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D007783:Lactones; D009690:Nucleic Acid Conformation; D011420:Propiolactone; D013950:Thymus Gland; D013997:Time Factors
C026371:5'-O-(2-carboxyethyl)phosphono-1-(2-carboxyethyl)deoxyadenosine; D004277:DNA, Single-Stranded; D003838:Deoxyadenine Nucleotides; D007783:Lactones; C008407:1-methyladenine; C026369:1-(2-carboxyethyl)adenine; D011420:Propiolactone; C026368:N(6)-(2-carboxyethyl)adenine; C026370:1-(2-carboxyethyl)deoxyadenosine 5'-monophosphate; D000225:Adenine