Nucleic Acids Research, 1984, Vol. 12, No. 13 5429-5439
© 1984
CHEMISTRY |
Two rotameric forms of open ring 7-methylguanine are present in alkylated polnucleotides
Unité de Biochimie et Enzymologie, Institut Gustave-Roussy 94805 Villejuif Cedex +Department de Chimie Organique des Sciences Pharmaceutiques et Biologiques INSERM U.266, CNRS ERA 613, 4 av. de l'Observatoire, 75006 Paris, France
Received April 26, 1984. Accepted June 1, 1984.
Righ performance liquid chromatography analysis of imidazole open ring 7-methylguanine, 2–6 diamino-4-hydroxy-5N-methyl-formamidopyrimidine (rom7G) showed two well-separated peaks (fI and fII) of the same magnitude. Rechromatography of each isolated component indicated that they are slowly interconverted to give a 1:1 mixture. NMR analysis demonstrated that the two species observed on reversed phase HPLC are rotational isomers. Thermodynamic measurements strongly suggested that the equilibrium can be assigned to rotation around the N-methyl fortnamido bond. The two species, fI and fII, separated by HPLC were identified as rotamers E and Z, respectively. The structures of fI and fII were also determined.
A polynucleotide containing rom7G was obtained by alkaline treatment of poly(dGC) containing 7-methylciuanine. In order to study its structure within the polynucleotide, rom7G was enzymatically excized by E.coli rom7G glycosylase. The analysis of the products released by the enzyme showed a 1:4 mixture of the two rotamers favoring the Z form (fII).
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