Synthesis of sulfo and sialyl Lewis(X) analogs with a mannose at the reducing end

被引:13
作者
Huang, BG [1 ]
Locke, RD [1 ]
Jain, RK [1 ]
Matta, KL [1 ]
机构
[1] ROSWELL PK CANC INST,DEPT GYNECOL ONCOL,BUFFALO,NY 14216
关键词
D O I
10.1016/S0960-894X(97)00181-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Stereoselective syntheses of 3-O-sulfo and 3-O-sialyl Lewis(X) analogs 1 and 2 were accomplished. Compound 1 showed greater inhibitory activity than the natural ligand sialyl Lewis(X) against P and L-selectin.
引用
收藏
页码:1157 / 1160
页数:4
相关论文
共 23 条
[1]  
ALLENSEN NM, 1994, TETRAHEDRON-ASYMMETR, V5, P2061
[2]  
DASGUPTA F, 1994, EXPERT OPIN INV DRUG, V3, P709
[3]   SYNTHESIS OF DEOXY-L-FUCOSE-CONTAINING SIALYL-LEWIS-X GANGLIOSIDE ANALOGS .56. SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES [J].
HASEGAWA, A ;
ANDO, T ;
KATO, M ;
ISHIDA, H ;
KISO, M .
CARBOHYDRATE RESEARCH, 1994, 257 (01) :67-80
[4]   SYNTHESIS OF BIOLOGICALLY-ACTIVE SIALYL-LEWIS-X MIMETICS [J].
HUANG, HM ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3100-3106
[5]   FURTHER CHARACTERIZATION OF THE INTERACTION BETWEEN L-SELECTIN AND ITS ENDOTHELIAL LIGANDS [J].
IMAI, Y ;
LASKY, LA ;
ROSEN, SD .
GLYCOBIOLOGY, 1992, 2 (04) :373-381
[6]   TOTAL SYNTHESIS OF 3'-O-SIALYL, 6'-O-SULFO LEWIS(X), NEUAC-ALPHA-2-]3(6-O-SO3NA)GA1-BETA-1-]4(FUC-ALPHA-1-]3)-GLCNAC-BETA-OME - A MAJOR CAPPING GROUP OF GLYCAM-I [J].
JAIN, RK ;
VIG, R ;
RAMPAL, R ;
CHANDRASEKARAN, EV ;
MATTA, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12123-12124
[7]   SYNTHETIC STUDIES IN CARBOHYDRATES .83. SYNTHESIS OF OLIGOSACCHARIDES CONTAINING THE X-ANTIGENIC TRISACCHARIDE (ALPHA-L-FUCP-(1-]3)-[BETA-D-GALP-(1-]4)]-BETA-D-GLCPNAC) AT THEIR NONREDUCING ENDS [J].
JAIN, RK ;
MATTA, KL .
CARBOHYDRATE RESEARCH, 1992, 226 (01) :91-100
[8]   Chemical synthesis of a hexasaccharide comprising the Lewis(x) determinant linked beta-(1->6) to a linear trimannosyl core and the precursor pentasaccharide lacking fucose [J].
Jain, RK ;
Matta, KL .
CARBOHYDRATE RESEARCH, 1996, 282 (01) :101-111
[9]  
JAIN RK, 1997, J CHEM SOC CHEM COMM, P23
[10]  
JAIN RK, 1996, J CHEM SOC CHEM COMM, P65