Deuterium Isotope Effect on Shifts of 13C Magnetic Resonance Signals of Sugars: Signal Assignment Studies

Abstract

The 13C chemical shifts of nuclei in several sugars undergo an isotope effect 0 to −0.10 p.p.m when a proton in the β position is substituted by a deuteron. The effect may be used for signal assignments in crowded spectra if it is taken into account that lower values are observed for 13C nuclei which are attached to more electronegative groups. The β effect coupled with the elimination of the α-carbon signal have been used to assign signals in c.m.r. spectra of the α- and β-anomers of D-glucose, D-mannose, D-allose, and D-galactose.