Oxidation of the primary hydroxyl group of galactose of galactaosyl ceramide analogue by chemical method-precursors for the synthesis of labeled conjugates

Sayuri Yonekawa; Clifford A Lingwood; Murugesapillai Mylvaganam

doi:10.1016/j.carres.2008.12.002

Oxidation of the primary hydroxyl group of galactose of galactaosyl ceramide analogue by chemical method-precursors for the synthesis of labeled conjugates

Carbohydr Res. 2009 Mar 10;344(4):501-6. doi: 10.1016/j.carres.2008.12.002. Epub 2008 Dec 11.

Authors

Sayuri Yonekawa¹, Clifford A Lingwood, Murugesapillai Mylvaganam

Affiliation

¹ Molecular Structure and Function, Research Institute, Hospital for Sick Children, Ontario, Canada.

PMID: 19144327
DOI: 10.1016/j.carres.2008.12.002

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%.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ceramides / chemistry*
Galactose / chemistry*
Iodobenzenes / chemistry
Isotope Labeling
Models, Chemical
Molecular Structure
Oxidation-Reduction
Spectrometry, Mass, Electrospray Ionization
Tandem Mass Spectrometry

Substances

Ceramides
Iodobenzenes
o-iodoxybenzoic acid
Galactose