BIOLOGICALLY-ACTIVE HEPARIN-LIKE FRAGMENTS WITH A NON-GLYCOSAMINO GLYCAN STRUCTURE .3. ORTHO-ALKYLATED-ORTHO-SULFATED PENTASACCHARIDES

被引：33

作者：

BASTEN, J

JAURAND, G

OLDEHANTER, B

DUCHAUSSOY, P

PETITOU, M

VANBOECKEL, CAA

机构：

[1] SANOFI RECH,9 RUE PRESIDENT SALVADOR ALLENDE,F-94256 GENTILLY,FRANCE

[2] ORGANON INT BV,5340 BH OSS,NETHERLANDS

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 09期

关键词：

D O I：

10.1016/S0960-894X(00)80585-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of analogues of biologically active heparin pentasaccharide fragments is reported. Replacement of N-sulphate by O-sulphate esters and introduction of various O-alkyl ethers resulted in biologically active "non-glycosamino" glycans. The biological activity can be further modulated by changing the nature and the position of the alkyl chains introduced.

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页码：905 / 910

页数：6

相关论文

共 10 条

[1] 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

[2] CONSTRUCTING A MOLECULAR-MODEL OF THE INTERACTION BETWEEN ANTITHROMBIN-III AND A POTENT HEPARIN ANALOG [J].

GROOTENHUIS, PDJ ;

VANBOECKEL, CAA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2743-2747

[3] THE ORIGIN OF THE SPECIFICITY IN THE RECOGNITION OF OLIGOSACCHARIDES BY PROTEINS [J].

LEMIEUX, RU .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (03) :347-374

[4] BUILDING-BLOCKS OF OLIGOSACCHARIDES .7. SYNTHESIS OF SELECTIVELY BLOCKED 2-AZIDO-2-DEOXY-D-GLUCOPYRANOSYL HALIDES AND D-GALACTOPYRANOSYL HALIDES - REACTIVITY AND C-13-NMR SPECTRA [J].

PAULSEN, H ;

RICHTER, A ;

SINNWELL, V ;

STENZEL, W .

CARBOHYDRATE RESEARCH, 1978, 64 (JUL) :339-362

[5] 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

[6] A NEW, HIGHLY POTENT, HEPARIN-LIKE PENTASACCHARIDE FRAGMENT CONTAINING A GLUCOSE RESIDUE INSTEAD OF A GLUCOSAMINE [J].

PETITOU, M ;

JAURAND, G ;

DERRIEN, M ;

DUCHAUSSOY, P ;

CHOAY, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (02) :95-98

[7] CONFORMATION OF THE PENTASACCHARIDE CORRESPONDING TO THE BINDING-SITE OF HEPARIN FOR ANTITHROMBIN-III [J].

RAGAZZI, M ;

FERRO, DR ;

PERLY, B ;

SINAY, P ;

PETITOU, M ;

CHOAY, J .

CARBOHYDRATE RESEARCH, 1990, 195 (02) :169-185

[8] SYNTHESIS OF TRISACCHARIDE AND TETRASACCHARIDE HAPTENS RELATED TO THE ASIALO FORMS OF THE GANGLIOSIDES GM2 AND GM1 [J].

SABESAN, S ;

LEMIEUX, RU .

CANADIAN JOURNAL OF CHEMISTRY, 1984, 62 (04) :644-654

[9]

VANBOECKEL CAA, 1987, RECL TRAV CHIM PAY B, V106, P581

[10] SYNTHESIS OF A POTENT ANTITHROMBIN ACTIVATING PENTASACCHARIDE - A NEW HEPARIN-LIKE FRAGMENT CONTAINING 2 3-O-SULPHATED GLUCOSAMINES [J].

VANBOECKEL, CAA ;

BEETZ, T ;

VANAELST, SF .

TETRAHEDRON LETTERS, 1988, 29 (07) :803-806