title: Oxidation of the primary hydroxyl group of galactose of galactaosyl ceramide analogue by chemical method-precursors for the synthesis of labeled conjugates.
abstract: Isotopic labeling of the C-6 of a model glycosphingolipid (2S, 3R, 4E)-2-(1-adamantanacetamido)-3-hydroxy-4-octadecenyl-beta-D-galactopyranoside, GalCAda, is described. Oxidation of (2S, 3R, 4E)-2-(1-adamantanacetamido)-3-(benzoyloxy)-4-octadecenyl-2,3,4-tri-O-benzoyl-beta-D-galactopyranoside with o-iodoxybenzoic acid gave the dialdoside derivative in good yield. Reduction of the dialdoside with sodium borodeuteride gave the deuterium labeled D-GalCAda, with a cumulative yield of 35%.
authors.affiliation: Molecular Structure and Function, Research Institute, Hospital for Sick Children, Ontario, Canada.
authors.forename: Sayuri
authors.initials: S
authors.lastname: Yonekawa
authors.forename: Clifford A
authors.initials: CA
authors.lastname: Lingwood
authors.forename: Murugesapillai
authors.initials: M
authors.lastname: Mylvaganam
mesh_terms: D002518:Ceramides / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry; D007553:Isotope Labeling; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
chemical_list: D002518:Ceramides; D007462:Iodobenzenes; C476101:o-iodoxybenzoic acid; D005690:Galactose