6-O-(10-undecyIenoyI)-D-Glucose: Controlled Enzymatic Synthesis and Structure Elucidation by ~1H and ~(13)C NMR

摘要

A direct esterification synthesis of glucose undecylenic acid sugar monoester is described, using the immobilized lipase enzyme NOVO-435 in 2-methyl-2-butonal and in ethyl methyl ketone (EMK). conditions were optimized in order to produce the monoester more rapidly and in higher yield. After the reaction product was purified, mass spectroscopy revealed that it had a molecular weight of 346.2 AMU. Further characterization by ~1H and ~(13)C NMR spectroscopy was carried out, including two-dimensional (2D) ~1H-~1H COSY and heteronuclear ~1H-~(13)C HSQC experiments. These data enabled identification of the monoester product to be 6-O-(10-undercylenoyl)a-D-glucose (74%), and 6-O-(10-undercylenoyl)P-D-glucose (26%) in methanol solution.