Abstract
To investigate the substrate specificity of β-L-rhamnosidase, the following β-L-rhamnopyranosides were synthesized: 1-(β-L-rhamnopyranosyl)-DL-glycerol (1), methyl β-L-rhamnopyranoside (2), methyl 2-O-(β-L-rhamnopyranosyl)-β-D-glucopyranoside (3) and methyl 2-O-(β-L-rhamnopyranosyl)-α-L-arabinopyranoside (4). The synthesis of 3 was performed using L-quinovose with neighboring group participation, which lead stereoselectively to the β-L-quinovoside. The 2-OH of the L-quinovo-unit was selectively deblocked, oxidized to the keto group, and then stereoselectively reduced, whereby 3 was produced.
