Optically pure 1-O- and 3-O-β-D-glucosyl- and galactosyl-sn-glycerols through lipase-catalyzed transformations

Pseudomonas cepacia lipase shows opposite stereoselectivity in the acylation versus the deacylation of diastereoisomeric 1-O- and 3-O-β-D-glycopyranosyl-sn-glycerols: while the 2,3,4,6-tetraacetylated 1-O-glycosyl-sn-glycerols were the preferred substrates in the former reaction, the 3-O-peracetylated derivatives were hydrolyzed in the latter one. In this way, both 1-O- and 3-O-stereoisomers could be obtained optically pure as residual substrates.