Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

被引:18
作者
Gouin, SG
Pilgrim, W
Porter, RK [1 ]
Murphy, PV
机构
[1] Univ Coll Dublin, Dept Biochem, Dublin 2, Ireland
[2] Univ Coll Dublin, Ctr Synth & Chem Biol, Dept Chem, Conway Inst Biomol & Biomed Res, Dublin 4, Ireland
基金
爱尔兰科学基金会;
关键词
mitochondrial uncoupling protein; glycoconjugates; glucose-O-omega-palmitic acid; palmitic acid; 16-(beta-D-glucopyranosyloxy)-hexadecanoic acid;
D O I
10.1016/j.carres.2005.04.004
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1547 / 1552
页数:6
相关论文
共 11 条
[1]   How do uncoupling proteins uncouple? [J].
Garlid, KD ;
Jaburek, M ;
Jezek, P ;
Varecha, M .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS, 2000, 1459 (2-3) :383-389
[2]   Structure and function of the uncoupling protein from brown adipose tissue [J].
Klingenberg, M ;
Huang, SG .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 1999, 1415 (02) :271-296
[3]   Structure-function relationship in UCP1 [J].
Klingenberg, M ;
Echtay, KS ;
Bienengraeber, M ;
Winkler, E ;
Huang, SG .
INTERNATIONAL JOURNAL OF OBESITY, 1999, 23 (Suppl 6) :S24-S29
[4]   CATALYTIC STEREOSELECTIVE SYNTHESIS OF 2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDES AND GALACTOPYRANOSIDES [J].
MATSUBARA, K ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1993, (12) :2145-2148
[5]   Sugar/steroid/sugar conjugates: Sensitivity of lipid binding to sugar structure [J].
Mbadugha, BNA ;
Menger, FM .
ORGANIC LETTERS, 2003, 5 (22) :4041-4044
[6]   Stereospecific synthesis of β-D-allopyrano sides by dihydroxylation of β-D-erythro-2,3-dideoxyhex-2-enopyranosides [J].
Murphy, PV ;
O'Brien, JL ;
Smith, AB .
CARBOHYDRATE RESEARCH, 2001, 334 (04) :327-335
[7]   THERMOGENIC MECHANISMS IN BROWN FAT [J].
NICHOLLS, DG ;
LOCKE, RM .
PHYSIOLOGICAL REVIEWS, 1984, 64 (01) :1-64
[8]   A history of the first uncoupling protein, UCP1 [J].
Nicholls, DG ;
Rial, E .
JOURNAL OF BIOENERGETICS AND BIOMEMBRANES, 1999, 31 (05) :399-406
[9]   Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid:: Stereoselective synthesis of glycosides and 2-deoxyglycosides [J].
Poláková, M ;
Pitt, N ;
Tosin, M ;
Murphy, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (19) :2518-2521
[10]   Evidence for cyclic bromonium ion transfer in electrophilic bromination of alkenes: Reaction of omega-alkenyl glycosides with aqueous N-bromosuccinimide [J].
Rodebaugh, R ;
FraserReid, B .
TETRAHEDRON, 1996, 52 (22) :7663-7678