title: Analysis of anomeric configurations in glyceroglycolipids and glycosphingolipids by chromium trioxide oxidation.
abstract: Acetylation and CrO(3) oxidation in acetic acid (Angyal and James, Aust. J. Chem. 23: 1209-1221, 1970) was applied to 18 different glyceroglycolipids and glycosphingolipids of known structure. The lipids studied contained from one to five pyranosic monosaccharide units including alpha- and beta-linked glucose, galactose, mannose, and N-acetylgalactosamine and beta-linked N-acetylglucosamine. Monosaccharides bound to the lipids through beta-glycosidic linkages reacted to the extent of 80-97 percent, but in the case of alpha-glycosidic linkages the oxidation proceeded only to the extent of 0-6 percent. A partial reaction was observed in lipids in which a given monosaccharide unit was present in both anomeric forms. Therefore, oxidation with CrO(3) allows the determination of anomeric configurations in simple glycolipids. Samples of only 100-300 mug are required.
mesh_terms: D001419:Bacteria / Q000032:analysis; D001923:Brain Chemistry; D002857:Chromium; D004075:Diglycerides / Q000032:analysis*; D004912:Erythrocytes / Q000032:analysis; D005989:Glycerides / Q000032:analysis*; D006017:Glycolipids / Q000032:analysis*; D006028:Glycosphingolipids / Q000032:analysis*; D006595:Hexosamines / Q000032:analysis; D008968:Molecular Conformation; D009005:Monosaccharides / Q000032:analysis; D010084:Oxidation-Reduction; D010087:Oxides; D010944:Plants / Q000032:analysis; D014908:Triticum / Q000032:analysis
chemical_list: D004075:Diglycerides; D005989:Glycerides; D006017:Glycolipids; D006028:Glycosphingolipids; D006595:Hexosamines; D009005:Monosaccharides; D010087:Oxides; D002857:Chromium