Synthesis and anti-thrombin activity of a hexasaccharide corresponding to the binding site of dermatan sulfate to heparin cofactor II

被引：9

作者：

Bourhis, P

Machetto, F

Duchaussoy, P

Herault, JP

Mallet, JM

Herbert, JM

Petitou, M

Sinay, P

机构：

[1] ECOLE NORMALE SUPER,DEPT CHIM,CNRS,URA 1686,F-75231 PARIS 05,FRANCE

[2] SANOFI RECH,HAEMOBIOL RES DEPT,F-31036 TOULOUSE,FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1997年 / 7卷 / 22期

关键词：

D O I：

10.1016/S0960-894X(97)10082-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new synthetic route is described toward the hexasaccharide representing the heparin cofactor II binding region of dermatan sulfate, The anti-thrombin activity of this synthetic hexasaccharide is reported here for the first time, This compound is about mio hundred times less active than dermatan sulfate itself for its ability to inhibit thrombin via heparin cofactor II. (C) 1997 Published by Elsevier Science Ltd.

引用

收藏

页码：2843 / 2846

页数：4

相关论文

共 18 条

[1] SYNTHESIS OF A DERMATAN SULFATE-LIKE HEXASACCHARIDE WITH A NON-GLYCOSAMINO GLYCAN STRUCTURE [J].

BASTEN, JEM ;

VANBOECKEL, CAA ;

JAURAND, G ;

PETITOU, M ;

SPIJKER, NM ;

WESTERDUIN, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (07) :893-898

[2] STRUCTURE-ACTIVITY RELATIONSHIP IN HEPARIN - A SYNTHETIC PENTASACCHARIDE WITH HIGH-AFFINITY FOR ANTI-THROMBIN-III AND ELICITING HIGH ANTI-FACTOR-XA ACTIVITY [J].

CHOAY, J ;

PETITOU, M ;

LORMEAU, JC ;

SINAY, P ;

CASU, B ;

GATTI, G .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1983, 116 (02) :492-499

[3]

DESS DB, 1991, J AM CHEM SOC, V113, P7227

[4] SYNTHESIS OF A DERMATAN SULFATE HEXASACCHARIDE THAT ACTIVATES HEPARIN-COFACTOR-II [J].

GOTO, F ;

OGAWA, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (04) :619-624

[5] SYNTHESIS OF DERMATAN SULFATE FRAGMENTS - A CHEMICAL SYNTHESIS OF METHYL 2-ACETAMIDO-2-DEOXY-3-O-(ALPHA-L-IDOPYRANOSYLURONIC ACID)-4-O-SULFO-BETA-D-GALACTOPYRANOSIDE DISODIUM SALT AND ITS NONSULFATED ANALOG [J].

JACQUINET, JC ;

SINAY, P .

CARBOHYDRATE RESEARCH, 1987, 159 (02) :229-253

[6]

JAURAND G, 1994, CARBOHYDR LETT, V1, P47

[7]

MACHETTO F, 1992, THESIS U PARIS 6

[8]

MAIMONE MM, 1990, J BIOL CHEM, V265, P18263

[9] ACTIVE-SITES OF DERMATAN SULFATE FOR HEPARIN-COFACTOR-II - ISOLATION OF A NONASACCHARIDE FRAGMENT CONTAINING 4 DISACCHARIDE SEQUENCES [ALPHA-L-IDURONIC ACID 2-O-SULFATE (1,3)-BETA-D-N-ACETYLGALACTOSAMINE 4-SULFATE] [J].

MASCELLANI, G ;

LIVERANI, L ;

PRETE, A ;

BERGONZINI, GL ;

BIANCHINI, P ;

SILVESTRO, L ;

TORRI, G ;

BISIO, A ;

GUERRINI, M ;

CASU, B .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (08) :1165-1177

[10] SYNTHESIS OF HEPARIN FRAGMENTS - A METHYL ALPHA-PENTAOSIDE WITH HIGH-AFFINITY FOR ANTITHROMBIN-III [J].

PETITOU, M ;

DUCHAUSSOY, P ;

LEDERMAN, I ;

CHOAY, J ;

JACQUINET, JC ;

SINAY, P ;

TORRI, G .

CARBOHYDRATE RESEARCH, 1987, 167 :67-75