title: Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins.
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.
authors.affiliation: Centre for Synthesis and Chemical Biology, Department of Chemistry, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Ireland.
authors.forename: Sebastien G
authors.initials: SG
authors.lastname: Gouin
authors.forename: Wayne
authors.initials: W
authors.lastname: Pilgrim
authors.forename: Richard K
authors.initials: RK
authors.lastname: Porter
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D000081:Acetamides; D002352:Carrier Proteins / Q000378:metabolism*; D062845:Chloroacetates; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007473:Ion Channels; D008565:Membrane Proteins / Q000378:metabolism*; D008928:Mitochondria / Q000378:metabolism*; D024101:Mitochondrial Proteins; D015394:Molecular Structure; D014238:Trichloroacetic Acid / Q000737:chemistry; D000071256:Uncoupling Protein 1
chemical_list: D000081:Acetamides; D002352:Carrier Proteins; D062845:Chloroacetates; D006017:Glycolipids; D007473:Ion Channels; D008565:Membrane Proteins; D024101:Mitochondrial Proteins; D000071256:Uncoupling Protein 1; D014238:Trichloroacetic Acid; C009528:trichloroacetamide