Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides.

Abstract:

:High 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 formamido 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-methylguanine. In order to study its structure within the polynucleotide, rom7G was enzymatically excized by E.coli rom7G-DNA glycosylase. The analysis of the products released by the enzyme showed a 1:4 mixture of the two rotamers favoring the Z form (fII).

journal_name

Nucleic Acids Res

journal_title

Nucleic acids research

authors

Boiteux S,Belleney J,Roques BP,Laval J

doi

10.1093/nar/12.13.5429

subject

Has Abstract

pub_date

1984-07-11 00:00:00

pages

5429-39

issue

13

eissn

0305-1048

issn

1362-4962

journal_volume

12

pub_type

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