Abstract
Tautomerism, protonation and electronic properties of the base moieties of IA′-metamorphosine ( 1a), N 2,3-ethenoguanosine ( 2a) and O 6-benzyl-N 2,3-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 N 2,3-ethenoguanosine and its 9-ethyl counterpart (7) were elucidated by phase distribution and potentiometric measurements.
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