A quantum-mechanical study of the interaction of glyoxal with guanine |
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Authors: | Daniel Demoulin Anne-Marie Armbruster Bernard Pullman |
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Institution: | (1) Institut de Biologie Physico-Chimique, National Foundation for Cancer Research, Regional Workshop, 13, rue P. et M. Curie, F-75005 Paris, France |
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Abstract: | A quantum molecular study by the SCFab initio method of the interaction of glyoxal with guanine provides for the formation of a stable covalent adduct in which the glyoxal
fragment forms a complementary cyclic ring attached to the imino N1 and amino N2 atoms of guanine with the concomitant migration of the N-bonded H atoms to the oxygens of glyoxal. The reaction should proceed
in two steps. The most plausible mechanism involves as the first step the interaction of a carbonyl group of glyoxal with
the amino group of guanine followed by a similar interaction at the imino group of guanine, rather than the reverse order
of interactions. The respective energy barriers are 49.7 and 63.9 kcal/mole. The intermediate product is also more stable
when the adduct occurs first at N2:30.7 kcal/mole versus 17.9 kcal/mole for the adduct at N1. |
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Keywords: | Glyoxal interaction of ∼ with guanine |
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