Computational Chemistry and Molecular Modeling
Atomic, Molecular and Optical Physics
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Infrared spectroscopy has been employed to study possible base pair interactions, in nonpolar media, between O6-methylguanine and uracil, cytosine and adenine; and between derivatives of N4-hydroxycytosine and adenine. The association constants of O6-methylguanine with uracil, cytosine, and adenine are well below 1M-1, whereas those for interaction of 1-methyl-N4-methoxycytosine and its 5-methyl derivative with adenine are identical, K = 14M-1. The significance of the latter finding is discussed in relation to the conformation of the exocyclic N4-methoxy group. Quantum chemical calculations, with the aid of the perturbation method, were carried out for the interaction of O6-methylguanine with uracil, cytosine, and adenine, to establish the most energetically favoured configurations for interactions of the free bases, and of the same base pairs in the B form of DNA. The role of the conformation of the exocyclic - OCH3 group in O6-methylguanine is discussed. The relevance of both the experimental and theoretical results to mutagenesis by O6-methylguanine and N4-hydroxycytosine is examined.
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