N23-ethenoguanosine and IA′-metamorphosine: 5N NMR spectroscopy and elucidation of physico-chemical properties by kinetic and equilibrium measurements

Article abstract of DOI:10.1016/S0040-4020(01)82321-8

Tautomerism, protonation and electronic properties of the base moieties of IA′-metamorphosine (1a), N²,3-ethenoguanosine (2a) and O⁶-benzyl-N²,3-ethenoguanosine (3a were investigated by ¹⁵N NMR spectroscopy. pK_a values of the same compounds were determined spectrophotometrically, and hydrolytic stability of the N-glycosidic bond was studied at various hydronium ion concentrations. The base stacking ability and metal ion complexation of N²,3-ethenoguanosine and its 9-ethyl counterpart (7) were elucidated by phase distribution and potentiometric measurements.