Collect. Czech. Chem. Commun. 1984, 49, 828-833

Chiroptical and conformational properties of ketohexoses

Slavomír Bystrický, Tibor Sticzay and Štefan Kučár

Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava


Circular dichroism of acyclic forms of D-fructose, L-sorbose, D-tagatose, and four deoxy derivatives of D-fructose has been interpreted from the point of view of the equilibrium of rotamers around the bond of the chromophore and chiral residue of the molecule. The conformational equilibrium manifested by the double-sign dichroic curve changes with constitutional, solvation, and temperature conditions. It can be characterized as a synanti equilibrium according to mutual orientation of the carbonyl and vicinal hydroxyl groups.