SPIROKETAL GLYCOMIMETICS - THE SYNTHESIS OF A CONFORMATIONALLY RESTRAINED SIALYL-LEWIS-X MIMIC

被引:22
作者
BIRKBECK, AA
LEY, SV
PRODGER, JC
机构
[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND
[2] GLAXO RES & DEV LTD,MED RES CTR,DEPT BIOMOLEC STRUCT,STEVENAGE SG1 2NY,HERTS,ENGLAND
关键词
D O I
10.1016/0960-894X(95)00469-A
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of a spiroketal scaffold and its specific elaboration with N-acetyl neuraminic acid and fucose monosaccharides to yield the conformationally restrained Sialyl Lewis X mimic 2 is described.
引用
收藏
页码:2637 / 2642
页数:6
相关论文
共 50 条
[1]   A NOVEL MIMIC OF THE SIALYL-LEWIS X DETERMINANT [J].
ALLANSON, NM ;
DAVIDSON, AH ;
MARTIN, FM .
TETRAHEDRON LETTERS, 1993, 34 (24) :3945-3948
[2]  
ALLANSON NM, 1994, TETRAHEDRON-ASYMMETR, V5, P261
[3]   SYNTHESIS AND STRUCTURAL-ANALYSIS USING 2-D NMR OF SIALYL LEWIS-X (SLE(X)) AND LEWIS-X (LE(X)) OLIGOSACCHARIDES - LIGANDS RELATED TO E-SELECTIN [ELAM-1] BINDING [J].
BALL, GE ;
ONEILL, RA ;
SCHULTZ, JE ;
LOWE, JB ;
WESTON, BW ;
NAGY, JO ;
BROWN, EG ;
HOBBS, CJ ;
BEDNARSKI, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5449-5451
[4]  
BAMFORD MJ, UNPUB BIOORG MED CHE
[5]  
BERG EL, 1991, J BIOL CHEM, V266, P14869
[6]  
BEVILACQUA MP, 1993, AN REV IMMUNOL, V11, P762
[7]  
BORMAN S, 1992, CHEM ENG NEWS, V70, P25, DOI 10.1021/cen-v070n031.p025
[8]   STRUCTURE-FUNCTION STUDIES ON SELECTIN CARBOHYDRATE LIGANDS - MODIFICATIONS TO FUCOSE, SIALIC-ACID AND SULFATE AS A SIALIC-ACID REPLACEMENT [J].
BRANDLEY, BK ;
KISO, M ;
ABBAS, S ;
NIKRAD, P ;
SRIVASATAVA, O ;
FOXALL, C ;
ODA, Y ;
HASEGAWA, A .
GLYCOBIOLOGY, 1993, 3 (06) :633-641
[9]   HYDROBORATION .71. HYDROBORATION OF REPRESENTATIVE HETEROCYCLIC OLEFINS WITH BORANE-METHYL SULFIDE, 9-BORABICYCLO[3.3.1]NONANE, DICYCLOHEXYLBORANE, AND DISIAMYLBORANE - SYNTHESIS OF HETEROCYCLIC ALCOHOLS [J].
BROWN, HC ;
PRASAD, JVNV ;
ZEE, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1582-1589
[10]   SIALYL LEWIS(X)-CONTAINING OLIGOSACCHARIDE ATTENUATES MYOCARDIAL REPERFUSION INJURY IN CATS [J].
BUERKE, M ;
WEYRICH, AS ;
ZHENG, ZL ;
GAETA, FCA ;
FORREST, MJ ;
LEFER, AM .
JOURNAL OF CLINICAL INVESTIGATION, 1994, 93 (03) :1140-1148