Raman spectra of methyl derivatives of 5′-adenosine monophosphate, tubercidin, inosine, uridine and cytidine. Perturbation of nucleoside vibrations by electrophilic attack at different sites☆

Add time:08/30/2019    Source:sciencedirect.com

Raman spectra have been obtained for 1-methyladenosine-5′-phosphate in H2O and D2O over a wide pH range, and its rearrangement in mild alkali to N6-methyladenosine-5′-phosphate has been followed. Similarly, the spectra of tubercidin (7-deazaadenosine) and 1-methyltubercidin were measured and the latter molecule also was observed to rearrange to the N6-derivative in base. The spectra of 7-methylinosine and of 1,7-dimethylinosine were obtained over a wide pH range in H2O and D2O as were the spectra of 3-methyluridine and 3-methylcytidine. The effect of methylation at different sites on the acidity and the spectra of nucleosides is discussed and compared with the effects of electrophilic attack by the proton, mercury(II) and platinum(II). The ring modes above 1500 cm−1 were observed to vary systematically depending upon the strength of the electrophile. The application of vibrational spectra to the assignment of the sites of electrophilic attack on nucleotides is discussed.

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