title: Regioselective hydrolysis of peracetylated alpha-D-glycopyranose catalyzed by immobilized lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis.
abstract: 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.
authors: Departamento de Biocatálisis, Instituto de Catálisis, Madrid, Spain.
authors: A
authors: A
authors: Bastida
authors: R
authors: R
authors: Fernández-Lafuente
authors: G
authors: G
authors: Fernández-Lorente
authors: J M
authors: JM
authors: Guisán
authors: G
authors: G
authors: Pagani
authors: M
authors: M
authors: Terreni
mesh_terms: 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
chemical_list: D004800:Enzymes, Immobilized; D009844:Oligosaccharides; D014867:Water; C105128:glucose pentaacetate; D008049:Lipase; D005947:Glucose