Synthesis of a S-linked heparan sulfate trisaccharide as the substrate mimic of heparanase

被引：25

作者：

Cao, HZ ^{[1
]}

Yu, B ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorg & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 25期

关键词：

heparan sulfate; S-linked oligosaccharide; glucuronic acid; glucosamine; glycosylation;

D O I：

10.1016/j.tetlet.2005.04.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

An approach to the Construction of the beta-(1 -> 4)-S-linkage between a glucuronic and a glucosamine unit, and then to the synthesis of a heparan sulfate trisaccharide containing such a linkage (1) as a nonhydrolyzable substrate mimic of heparanase was developed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4337 / 4340

页数：4

共 32 条

[1]

SYNTHESIS OF A THIO ANALOG OF N-PROPYL KOJIBIOSIDE, A POTENTIAL GLUCOSIDASE INHIBITOR [J].

ANDREWS, JS ;

PINTO, BM .

CARBOHYDRATE RESEARCH, 1995, 270 (01) :51-62

[2]

Heparanases: endoglycosidases that degrade heparan sulfate proteoglycans [J].

Bame, KJ .

GLYCOBIOLOGY, 2001, 11 (06) :91R-98R

[3]

BAYLEY H, 1978, TETRAHEDRON LETT, P3633

[4]

THE THIAZOLINE RING AS A PROTECTIVE GROUP OF 2-AMINO-2-DEOXY-3-THIO-MANNOSE [J].

BROSSMER, R ;

MACK, H .

TETRAHEDRON LETTERS, 1981, 22 (10) :933-936

[5]

Capila I, 2002, ANGEW CHEM INT EDIT, V41, P391

[6]

Conrad H.E., 1998, HEPARIN BINDING PROT

[7]

Heparanase, a potential regulator of cell-matrix interactions [J].

Dempsey, LA ;

Brunn, GJ ;

Platt, JL .

TRENDS IN BIOCHEMICAL SCIENCES, 2000, 25 (08) :349-351

[8]

DRIGUEZ H, 1997, TOP CURR CHEM, V187, P86

[9]

Synthesis of a thio-linked Lewis A (Lea) epitope [J].

Eisele, T ;

Windmüller, R ;

Schmidt, RR .

CARBOHYDRATE RESEARCH, 1998, 306 (1-2) :81-91

[10]

Fairweather J.K., 2000, CARBOHYDRATES CHEM B, V1, P531

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