Tautomeric transition in uracil and thymine nucleosides induced by deprotonated carboxylic group: <sup>1</sup>H NMR data

Svitlana P. Samijlenko; Andriy V. Stepanyugin; Andriy L. Potyahaylo; Dmytro M. Hovorun

doi:10.1117/12.570015

20 July 2004 Tautomeric transition in uracil and thymine nucleosides induced by deprotonated carboxylic group: ¹H NMR data

Svitlana P. Samijlenko, Andriy V. Stepanyugin, Andriy L. Potyahaylo, Dmytro M. Hovorun

Author Affiliations +

Proceedings Volume 5507, XVI International Conference on Spectroscopy of Molecules and Crystals; (2004) https://doi.org/10.1117/12.570015
Event: XVI International Conference on Spectroscopy of Molecules and Crystals, 2003, Sevastopol, Ukraine

Abstract

In ¹H NMR spectra of four nucleosides of uracil and thymine - U, dU, T and rT - in anhydrous DMSO in the presence of carboxylate-ion there was observed disappearance of signals of the N3H aglycon protons and all the hydroxyl protons of glycosylic fragments. This changes were interpreted as a result of the N3H - 02H proton transfer in the base residues under the complex formation between nucleosides and ligand molecules: one carboxylate-ion forms two H-bonds with groups 02H and 05'H, another - two H-bonds with hydroxyl groups 02'H and 03'H in the case of a riboside or one Hbond with group 03'H of a deoxyriboside. Orders ofthe complexes' stability were established, which from, particularly, the conclusion was drawn that the canonical nucleosides U and T form more stable complexes with carboxylate-ion, than metabolites dU and rT. Biological significance ofthe results obtained is pointed out.

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Svitlana P. Samijlenko, Andriy V. Stepanyugin, Andriy L. Potyahaylo, and Dmytro M. Hovorun "Tautomeric transition in uracil and thymine nucleosides induced by deprotonated carboxylic group: ¹H NMR data", Proc. SPIE 5507, XVI International Conference on Spectroscopy of Molecules and Crystals, (20 July 2004); https://doi.org/10.1117/12.570015

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