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Spectroscopic kinetic and semiempirical molecular orbital studies on 8 aminoadenosines 8 methylaminoadenosines and 8 dimethylaminoadenosines


, : Spectroscopic kinetic and semiempirical molecular orbital studies on 8 aminoadenosines 8 methylaminoadenosines and 8 dimethylaminoadenosines. Tetrahedron 47(26): 4693-4708

Kinetic studies on acidic depurination of 8-aminoadenosine, 8-methylaminoadenosine, and 8-dimethylaminoadensine show their relative rates are respectively 2.7, 2 and 429-fold with respects to adenosine. Structural consequence of 8-amino, 8-methylamino or 8-dimethylamino group in the 8-substituted purine nucleosides have been therefore investigated in order to delineate the influence of these 8-amino substitutents on the relative rate of cleavage of glycosyl bond under acidic condition by both 15N- and 1H-NMR spectroscopy in neutral and acidic solutions. 15N-NMR studies showed that the relative amount of protonation at N1 in 8-amino adenosine and 8-methylaminoadenosine are 66% (44% N7H+) and 85% (15% N7H+), respectively, while it is 66% (4% N7H+) in case of 8-dimethylaminoadenosine. 1H-NMR studies also showed some differences in conformation of sugar moiety of nucleosides in acidic solution in comparison with their conformations in neutral solution. Semiempirical Molecular Oribital calculations have been used to throw light on steric and electronic factors dictated by 8-amino, 8-methylamino or 8-dimethylamino group across C8-N8 bond that control the stabilization of N7H+ versus N1H+ species. Results from these Semiempirical Molecular Orbital calculations have been subsequently assessed with those obtained by 15N-NMR-studies.

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