SYNTHESIS OF A 6-O-PHOSPHORYLATED ANALOG OF THE ANTITHROMBIN-III BINDING SEQUENCE OF HEPARIN - REPLACEMENT OF ONE ESSENTIAL SULFATE GROUP BY A PHOSPHATE GROUP NULLIFIES THE BIOLOGICAL-ACTIVITY

被引:10
作者
VOS, JN
WESTERDUIN, P
VANBOECKEL, CAA
机构
[1] Akzo Pharma Division, Organon Scientific Development Group, 5340 BH Oss
关键词
D O I
10.1016/S0960-894X(01)80786-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of an analogue (i.e. compound 7) of the AT-III binding sequence of heparin is described in which an essential 6-O-SO3 group at the non-reducing glucosamine is replaced by a phosphate group. This compound appears to be biologically inactive.
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页码:143 / 146
页数:4
相关论文
共 14 条
[1]  
Choay J, 1981, Ann N Y Acad Sci, V370, P644, DOI 10.1111/j.1749-6632.1981.tb29770.x
[2]  
GROOTENHUIS PDJ, IN PRESS J AM CHEM S
[3]   HIGH SPECIFICITY OF A PHOSPHATE-TRANSPORT PROTEIN DETERMINED BY HYDROGEN-BONDS [J].
LUECKE, H ;
QUIOCHO, FA .
NATURE, 1990, 347 (6291) :402-406
[4]  
PETITOU M, 1987, CARBOHYD RES, V67, P167
[5]  
PETITOU M, 1989, HEPARIN CHEM BIOL PR, P65
[6]  
REITZ AB, IN PRESS INOSITOL PH
[7]   FURTHER CHARACTERIZATION OF THE ANTITHROMBIN-BINDING SEQUENCE IN HEPARIN [J].
THUNBERG, L ;
BACKSTROM, G ;
LINDAHL, U .
CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :393-410
[8]  
VANBOECKEL CAA, 1989, ANN NY ACAD SCI, V556, P489
[9]  
VANBOECKEL CAA, 1989, AUG EUROCARB 5 PRAG
[10]  
VANBOEKCEL CAA, 1988, TETRAHEDRON LETT, P803