Synthesis of fluorescence labeled sialyl Lewisx glycosphingolipids

被引:28
作者
Gege, C
Oscarson, S
Schmidt, RR
机构
[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
[2] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
关键词
D O I
10.1016/S0040-4039(00)01995-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The pyrene and nitrobenzoxadiazole (NBD) labeled derivatives of the natural sialyl Lewis(X) glycosphingolipid 1 were chemically synthesized as targets for investigating microdomain formation in membranes. The fluorescent analogs 2 and 3 were prepared by replacing the natural amide-linked fatty acid with a fluorescent analog. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:377 / 380
页数:4
相关论文
共 31 条
[1]   SYNTHESIS OF FLUORESCENT AND RADIOACTIVE ANALOGS OF 2 LACTOSYLCERAMIDES AND GLUCOSYLCERAMIDE CONTAINING BETA-THIOGLYCOSIDIC BONDS THAT ARE RESISTANT TO ENZYMATIC DEGRADATION [J].
ALBRECHT, B ;
PUTZ, U ;
SCHWARZMANN, G .
CARBOHYDRATE RESEARCH, 1995, 276 (02) :289-308
[2]   Lateral organization of pyrene-labeled lipids in bilayers as determined from the deviation from equilibrium between pyrene monomers and excimers [J].
Barenholz, Y ;
Cohen, T ;
Haas, E ;
Ottolenghi, M .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (06) :3085-3090
[3]  
Castro-Palomino J. C., 1997, ANGEW CHEM, V109, P2081
[4]   Efficient synthesis of ganglioside GM2 for use in cancer vaccines [J].
CastroPalomino, JC ;
Ritter, G ;
Fortunato, SR ;
Reinhardt, S ;
Old, LJ ;
Schmidt, RR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (18) :1998-2001
[5]   N-Trichloroethoxycarbonyl-glucosamine derivatives as glycosyl donors [J].
Dullenkopf, W ;
CastroPalomino, JC ;
Manzoni, L ;
Schmidt, RR .
CARBOHYDRATE RESEARCH, 1996, 296 :135-147
[6]   Guanidine/guanidinium nitrate; A mild and selective O-deacetylation reagent that leaves the N-Troc group intact. [J].
Ellervik, U ;
Magnusson, G .
TETRAHEDRON LETTERS, 1997, 38 (09) :1627-1628
[7]   CHEMICALLY-INDUCED PHASE SEPARATION IN MIXED VESICLES CONTAINING PHOSPHATIDIC-ACID - OPTICAL STUDY [J].
GALLA, HJ ;
SACKMANN, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (14) :4114-4120
[8]   EXCIMER-FORMING LIPIDS IN MEMBRANE RESEARCH [J].
GALLA, HJ ;
HARTMANN, W .
CHEMISTRY AND PHYSICS OF LIPIDS, 1980, 27 (03) :199-219
[9]  
GAREGG PJ, 1982, CARBOHYD RES, V108, P97
[10]  
Gege C, 2000, CHEM-EUR J, V6, P111, DOI 10.1002/(SICI)1521-3765(20000103)6:1<111::AID-CHEM111>3.0.CO