An explanation of the induction of mutations by 2-aminopurine from an ab initio molecular orbital study.
The molecular mechanism of induction of mutations by 2-aminopurine (AP) was studied by an ab initio molecular orbital method. Cytosine (C) is converted to its disfavored imino tautomer more easily than AP, judging from the calculated total energies of the bases and the base analogue. This suggests that a stable AP:C base mispair via two hydrogen bonds can be formed with the imino tautomer of C. These results stress the importance of the imino form of C in AP-induced mutagenesis and support the 'trigger mechanism', in which formation of one hydrogen bond between AP and C is considered to stimulate the tautomeric shift of AP or C. The calculated relative stabilities of various base pairs and mispairs were in good agreement with experimental findings.
D015075:2-Aminopurine / Q000494:pharmacology*; D000225:Adenine / Q000031:analogs & derivatives*; D001482:Base Composition; D055598:Chemical Phenomena; D002621:Chemistry; D003596:Cytosine; D004247:DNA; D006860:Hydrogen Bonding; D009153:Mutagens; D009154:Mutation
D009153:Mutagens; D015075:2-Aminopurine; D003596:Cytosine; D004247:DNA; D000225:Adenine