Preparation and properties of a coniferin enantiomer

Abstract

l-Coniferin (1L), which is an enantiomer of natural coniferin (d-coniferin (1D)), was prepared from l-glucose according to the conventional method for compound 1D. The reactivity of l-glucose and its derivatives was found to be almost same as that of the corresponding d-glucose and its derivatives during the preparation for compound 1L. Compound 1L showed resistance toward enzymatic hydrolysis by commercial β-glucosidase from Almond. However, unlike compound 1D, compound 1L was not transported across the membrane obtained from differentiating xylem of a hybrid poplar in the present assay. The result suggested for the first time that the d-/l-configuration of the glucose moiety of coniferin is an important factor affecting coniferin transport across the membrane.