Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues

Abstract

A theoretical and experimental characterization of N(1)-(2 0 ,3 0 -dihydroxypropil)thymine (DHPT), a potential prebiotic nucleoside analogue of 5-methyluridine, is performed. A proposed methodology based on a solvation method was used to study conformational transformations of the different low-energy conformers of DHPT according to time-dependent IR spectroscopy. NMR and CD spectroscopy provides additional evidence of these transformations. The conformational transformations appear to be due to solvent and DHPT interactions. This highlights the importance of experimental conditions on conformer ratio equilibrium, in particular, the interpretation of experimental conditions used for determining the stereoisomers' absolute configuration. K E Y W O R D S conformational transformations, nucleoside analogues, stereoisomers