Characteristic ¹H NMR spectra of β-d-ribofuranosides and ribonucleosides: factors driving furanose ring conformations.

ABSTRACT: A series of β-d-ribofuranosides and ribonucleosides fused with 2,3-O-isopropylidene ring was synthesized and studied in terms of their conformational preferences. Based on the ¹H NMR spectra, DFT calculations, and X-ray analysis the E ₀-like and E ₄-like conformations adopted by these furanosides are identified. The ³ E-like and ² E-like conformations are assigned to ribonucleosides without the 2,3-O-isopropylidene group. The studies are supported by analysis of the structural data of β-d-ribofuranosides and ribonucleosides deposited in the Cambridge Crystallographic Data Center (CCDC) database. Finally, the factors influencing the conformational preferences of the furanose ring with the β-d-ri

SUBMITTER: Walczak D 

PROVIDER: S-EPMC9557318 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature