Recent advances in the synthetic studies of glycosaminoglycans

被引：18

作者：

Tamura, J ^{[1
]}

机构：

[1] Tottori Univ, Fac Educ & Reg Sci, Tottori 6808551, Japan

来源：

TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY | 2001年 / 13卷 / 69期

关键词：

proteoglycan; glycosaminoglycan; chondroitin sulfate; dermatan sulfate; hyaluronic acid; heparin; heparan sulfate;

D O I：

10.4052/tigg.13.65

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The biological importance of the proteoglycan (PG) is increasing along with the elucidation of the biological properties. It is essential to approach it from synthetic chemistry in order to recognize the roles of PG at a molecular level. This review focuses on and generally surveys recent syntheses of glycosaminoglycan (GAG), a glycan part of PG, especially of the oligosaccharide at the linkage region of GAG, chondroitin sulfate, dermatan sulfate, hyaluronic acid and heparin / heparan sulfate.

引用

页码：65 / 88

页数：24

共 60 条

[1] n-pentenyl glycosyl orthoesters as versatile intermediates in oligosaccharide synthesis.: The proteoglycan linkage region [J].

Allen, JG ;

Fraser-Reid, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :468-469

[2] Syntheses of chondroitin 4-and 6-sulfate pentasaccharide derivatives having a methyl β-D-glucopyranosiduronic acid at the reducing end [J].

Bélot, F ;

Jacquinet, JC .

CARBOHYDRATE RESEARCH, 2000, 326 (02) :88-97

[3] Unexpected stereochemical outcome of activated 4,6-O-benzylidene derivatives of the 2-deoxy-2-trichloroacetamido-D-galacto series in glycosylation reactions during the synthesis of a chondroitin 6-sulfate trisaccharide methyl glycoside [J].

Bélot, F ;

Jacquinet, JC .

CARBOHYDRATE RESEARCH, 2000, 325 (02) :93-106

[4] The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of hyaluronic acid-related tetra-, hexa-, and octa-saccharides having a methyl beta-D-glucopyranosiduronic acid at the reducing end [J].

Blatter, G ;

Jacquinet, JC .

CARBOHYDRATE RESEARCH, 1996, 288 :109-125

[5] Synthesis and anti-thrombin activity of a hexasaccharide corresponding to the binding site of dermatan sulfate to heparin cofactor II [J].

Bourhis, P ;

Machetto, F ;

Duchaussoy, P ;

Herault, JP ;

Mallet, JM ;

Herbert, JM ;

Petitou, M ;

Sinay, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (22) :2843-2846

[6] Synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside disodium salts, related to heparin biosynthesis [J].

Cipolla, L ;

Nicotra, F ;

Lay, L ;

Lindahl, U ;

Panza, L ;

Russo, G .

GLYCOCONJUGATE JOURNAL, 1996, 13 (06) :995-1003

[7] 2-DEOXY-2-TRICHLOROACETAMIDO-D-GLUCOPYRANOSE DERIVATIVES IN OLIGOSACCHARIDE SYNTHESIS - FROM HYALURONIC-ACID TO CHONDROITIN 4-SULFATE TRISACCHARIDES [J].

COUTANT, C ;

JACQUINET, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1573-1581

[8] An unusual example of steric buttressing in glycosylation [J].

Crich, D ;

Dudkin, V .

TETRAHEDRON LETTERS, 2000, 41 (30) :5643-5646

[9] Influence of core protein sequence on glycosaminoglycan assembly [J].

Esko, JD ;

Zhang, LJ .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 1996, 6 (05) :663-670

[10]

FRITZ TA, 1994, J BIOL CHEM, V269, P300

← 1 2 3 4 5 6 →