Chemical and biochemical studies on carbohydrate esters. X. Plant growth inhibition by pure anomers of synthetic 1-O-lauroyl-D-glucopyranose.

Abstract

Anomerically pure, synthetic 1-O-lauroyl-α-and-β-D-glucopyranoses exhibited strong plant growth inhibiting activity in the Avena coleoptile straight growth test at a final concentration of 500/3 ppm. The growth inhibition ratios obtained with α-and β-anomers were 94.2% and 81.6%, respectively. Under the same conditions, 2-O-and 4-O-lauroyl-D-glucopyranoses and the mono-, di-, and poly-substituted products obtained by selective lauroylation of maltose were all found to be ineffective. In view of these results, the presence of a lauroyl function, either axial or equatorial, at the C-1 position of a monosaccharide unit appears to be important for this biological activity.