Two rotameric forms of open ring 7-methylguanine are present in alkylated polnucleotides | Zendy

Serge Boiteux | Zendy; Joël Belleney | Zendy; Bernárd P. Roques | Zendy; Jacques Laval | Zendy

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

Author(s) -

Serge Boiteux,

Joël Belleney,

Bernárd P. Roques,

Jacques Laval

Publication year - 1984

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/12.13.5429

Subject(s) - biology , alkylation , ring (chemistry) , stereochemistry , biochemistry , chemistry , organic chemistry , catalysis

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).

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