title: A novel chemical procedure for the selective removal of nonreducing terminal N-acetyl hexosamine residues from glycolipids.
abstract: A two-step oxidative hydrolysis procedure is described for the selective removal of nonreducing terminal N-acetylhexosamine residues from glycolipids. The procedure gives a 50-60% yield of the n-1 hexosyl ceramide, the remainder being peeling products (n-2, n-3, etc.). The reaction is dependent on the selective deacetylation of nonreducing terminal N-acetyl hexosamine residues by aqueous base hydrolysis. Deglycosylation then occurs in the presence of hydrogen peroxide. Glycolipids containing internal or no N-acetylhexosamine residues are unaltered in these reactions. This method is suitable for the large-scale deglycosylation of appropriate glycolipids and may also be used as an adjunct in structural determination of unknown amino sugar-containing glycolipids.
authors.affiliation: Department of Microbiology, Hospital for Sick Children, Toronto, Ontario, Canada.
authors.forename: C A
authors.initials: CA
authors.lastname: Lingwood
authors.forename: A
authors.initials: A
authors.lastname: Nutikka
mesh_terms: D000107:Acetylation; D002240:Carbohydrate Sequence; D005915:Globosides / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry*; D006595:Hexosamines / Q000737:chemistry*; D006801:Humans; D006868:Hydrolysis; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013997:Time Factors; D014281:Trihexosylceramides / Q000737:chemistry
chemical_list: D005915:Globosides; D006017:Glycolipids; D006595:Hexosamines; D009844:Oligosaccharides; D014281:Trihexosylceramides; C024032:globotetraosylceramide; C018549:globotriaosylceramide