Conformational analysis of the deoxyribofuranose ring: a theoretical study

Abstract

The results of energy calculations by the Consistent Force Field method for methyl β-D-2-deoxyribofuranoside are presented. Two regions of stable pentose conformations are predicted; within each region local energy minima are associated with different conformations of the hydroxy and hydroxymethylene groups. A conformational model of the molecule in solution is proposed. Proton coupling constants are calculated for the stable conformers found, and a qualitative agreement with the experimentally observed solution behaviour is achieved. The influence of the nature and conformation of exocyclic substituents on the conformation of the furanose ring and on the interconversion of conformations by pseudorotation is discussed.