Oxidation of the primary hydroxyl group of galactose of galactaosyl ceramide analogue by chemical method-precursors for the synthesis of labeled conjugates.
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%.
Yonekawa
Sayuri
S
Molecular Structure and Function, Research Institute, Hospital for Sick Children, Ontario, Canada.
Lingwood
Clifford A
CA
Mylvaganam
Murugesapillai
M
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
D002518:Ceramides; D007462:Iodobenzenes; C476101:o-iodoxybenzoic acid; D005690:Galactose