Protonation Sites of Adenine Derivatives. I. Nuclear Magnetic Resonance Investigation of Adenine N-3 Derivatives in Dimethyl Sulfoxide-d_6

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The protonation sites of adenine N-3 derivatives in dimethyl sulfoxide (DMSO)-d_6 were investigated on the basis of proton nuclear magnetic resonance (PMR) and carbon-13 nuclear magnetic resonance (^<13>C NMR) spectral measurements. The spectra of the protonated and non-protonated adenine N-3 derivatives showed that, upon protonation : 1) the chemical shift of the H-8 proton moved further downfield than that of the H-2 proton, and 2) the signal of NH_2 protons was split into a doublet at 30℃ and showed a broad line at 70℃, and 3) the signal of the C-5 carbon moved further upfield than that of the C-4 carbon. The findings indicate that adenine N-3 derivatives are protonated at the N-7 site.
公益社団法人日本薬学会の論文
1981-09-25