Enzymatic regioselective deprotection of peracetylated mono-and disaccharides
Gardossi, L.; Khan, R.; Konowicz, P.A.; Gropen, L.; Paulsen, B.S.
Journal of Molecular Catalysis B Enzymatic 6(1-2): 89-94
ISSN/ISBN: 1381-1177 DOI: 10.1016/s1381-1177(98)00130-1
Selective enzymatic hydrolysis of the peracetylated disaccharides, namely cellobiose, lactose, maltose and melibiose, with lipase from Asperilligus niger in aqueous buffer and organic solvent for 30 min afforded exclusively the corresponding heptaacetates with a free hydroxyl group at C-1 in high yield. Prolonged reaction of the beta-1,4 linked cellobiose and lactose peracetates afforded selectively their hexaacetates with free hydroxyl groups at C-1,2, whereas the alpha-1,4 linked disaccharides maltose and melibiose peracetate gave a complex mixture of products. The reaction of 2-acetamido-2-deoxy-1,3,4,6-tetra-O-acetylglucopyranose (11) for 22 h afforded as the major product the diacetate 12 with free hydroxyl groups at C-1,4.