Synthesis, photochemistry and enzymology of 2-O-(2-nitrobenzyl)-D-glucose, a photolabile derivative of D-glucose

Abstract

Alkylation of the dibutylstannylene derivative of methyl 4,6-O-benzylidene-α-D-glucopyranoside 2a with 2-nitrobenzyl bromide gave a mixture of 2-O- and 3-O-(2-nitrobenzyl) derivatives 3b and 4b in the ratio ∼ 3 : 1. Chromatographic separation and removal of the protecting groups gave the title compound 1. Regiospecific synthesis by 2-nitrobenzylation of the monoalcohol 8a was examined but could not be achieved efficiently. Compound 1 was neither a substrate for nor an inhibitor of the coupled hexokinase/glucose-6-phosphate dehydrogenase enzyme system. On photolysis, it was converted into free glucose with 1 : 1 stoichiometry.