NMR Quantification of Tautomeric Populations in Biogenic Purine Bases

Purine bases such as purine, adenine, hypoxanthine, and mercaptopurine are known to exist in several tautomeric forms. Characterization of their tautomeric equilibria is important not only for predicting the regioselectivity of their N-alkylation reactions but also for gaining knowledge of the patterns with which these compounds of significant biological activity form hydrogen bonds with their biological targets. Low-temperature 1H- and 13C-NMR spectroscopy were used to investigate the tautomeric equilibria for purine and some purine derivatives in methanol and N,N-dimethylformamide solutions. The N(7)H and N(9)H tautomeric forms were quantified by integrating the individual 1H NMR signals …