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

Sebastien G. Gouin
, Wayne Pilgrim
, Richard K. Porter
, Paul V. Murphy

University College Dublin
Trinity College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

20 Citations (Scopus)

Abstract

Glucose-O-ω-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.

Original language	English
Pages (from-to)	1547-1552
Number of pages	6
Journal	Carbohydrate Research
Volume	340
Issue number	8
DOIs	https://doi.org/10.1016/j.carres.2005.04.004
Publication status	Published - 13 Jun 2005
Externally published	Yes

Keywords

16-(β-d-Glucopyranosyloxy)-hexadecanoic acid
Glucose-O-ω-palmitic acid
Glycoconjugates
Mitochondrial uncoupling protein
Palmitic acid

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10.1016/j.carres.2005.04.004

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title = "Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins",

abstract = "Glucose-O-ω-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.",

keywords = "16-(β-d-Glucopyranosyloxy)-hexadecanoic acid, Glucose-O-ω-palmitic acid, Glycoconjugates, Mitochondrial uncoupling protein, Palmitic acid",

author = "Gouin, \{Sebastien G.\} and Wayne Pilgrim and Porter, \{Richard K.\} and Murphy, \{Paul V.\}",

year = "2005",

month = jun,

day = "13",

doi = "10.1016/j.carres.2005.04.004",

language = "English",

volume = "340",

pages = "1547--1552",

journal = "Carbohydrate Research",

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TY - JOUR

T1 - Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

AU - Gouin, Sebastien G.

AU - Pilgrim, Wayne

AU - Porter, Richard K.

AU - Murphy, Paul V.

PY - 2005/6/13

Y1 - 2005/6/13

N2 - Glucose-O-ω-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.

AB - Glucose-O-ω-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.

KW - 16-(β-d-Glucopyranosyloxy)-hexadecanoic acid

KW - Glucose-O-ω-palmitic acid

KW - Glycoconjugates

KW - Mitochondrial uncoupling protein

KW - Palmitic acid

UR - https://www.scopus.com/pages/publications/19344367310

U2 - 10.1016/j.carres.2005.04.004

DO - 10.1016/j.carres.2005.04.004

M3 - Article

SN - 0008-6215

VL - 340

SP - 1547

EP - 1552

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 8

ER -

Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

Abstract

Keywords

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