Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

Sebastien G Gouin; Wayne Pilgrim; Richard K Porter; Paul V Murphy

doi:10.1016/j.carres.2005.04.004

Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

Carbohydr Res. 2005 Jun 13;340(8):1547-52. doi: 10.1016/j.carres.2005.04.004.

Authors

Sebastien G Gouin¹, Wayne Pilgrim, Richard K Porter, Paul V Murphy

Affiliation

¹ Centre for Synthesis and Chemical Biology, Department of Chemistry, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Ireland.

PMID: 15885669
DOI: 10.1016/j.carres.2005.04.004

Abstract

Glucose-O-omega-palmitic acid is an amphipathic molecule that is useful as a tool for studying the mechanism of mitochondrial uncoupling proteins. The synthesis of this glycolipid is described herein. The study of the reaction of a series of glycosyl donors with appropriate acceptors derived from 16-hydroxyhexadecanoic acid showed that a glycosyl trichloroacetimidate donor was more efficient than thioglycoside, glycosyl halide and glycosyl acetate donors for synthesis of this glycolipid.

Publication types

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

MeSH terms

Acetamides
Carrier Proteins / metabolism*
Chloroacetates
Glycolipids / chemical synthesis*
Glycolipids / chemistry
Glycosylation
Ion Channels
Membrane Proteins / metabolism*
Mitochondria / metabolism*
Mitochondrial Proteins
Molecular Structure
Trichloroacetic Acid / chemistry
Uncoupling Protein 1

Substances

Acetamides
Carrier Proteins
Chloroacetates
Glycolipids
Ion Channels
Membrane Proteins
Mitochondrial Proteins
Uncoupling Protein 1
Trichloroacetic Acid
trichloroacetamide