Regioselective hydrolysis of peracetylated alpha-D-glycopyranose catalyzed by immobilized lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis.
Penta-O-acetyl-alpha-D-glucopyranose was selectively deacetylated in aqueous media by lipases from Candida cilindracea (CCL) adsorbed on octyl-agarose support. Enzymatic hydrolyses was regioselective at the 4-position under neutral pH and towards the 6 position under acidic conditions. This enzymatic approach allows the one step synthesis of 1,2,3,6-tetra-O-acetyl-alpha-D-glucopyranoses 1, a useful intermediate in oligosaccharide synthesis.
Bastida
A
A
Departamento de Biocatálisis, Instituto de Catálisis, Madrid, Spain.
Fernández-Lafuente
R
R
Fernández-Lorente
G
G
Guisán
J M
JM
Pagani
G
G
Terreni
M
M
D002236:Carbohydrate Conformation; D002384:Catalysis; D004800:Enzymes, Immobilized / Q000378:metabolism*; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014867:Water / Q000737:chemistry
D004800:Enzymes, Immobilized; D009844:Oligosaccharides; D014867:Water; C105128:glucose pentaacetate; D008049:Lipase; D005947:Glucose