Some key experimental features of a modular synthesis of heparin-like oligosaccharides

被引:49
作者
de Paz, JL [1 ]
Ojeda, R [1 ]
Reichardt, N [1 ]
Martín-Lomas, M [1 ]
机构
[1] Inst Invest Quim, CSIC, Grp Carbohidratos, Seville 41092, Spain
关键词
carbohydrates; glycosylation; heparin; oligosaccharides; synthesis design;
D O I
10.1002/ejoc.200300210
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The key features of a modular n+2 strategy for a completely stereoselective synthesis of oligosaccharides containing the GlcN-IdoA repeating unit of the major sequence of heparin are presented and discussed in detail. These key features include the regio- and stereoselective synthesis of disaccharide building blocks and the reactivity of building blocks in the modular assembly process. The synthetic strategy, the effectiveness of which has previously been demonstrated by the total synthesis of four hexasaccharides and two octasaccharides, allows the size and the charge distribution of the target oligosaccharide fragments to be controlled. (C) Wiley-VCH Verlag GmbH Co.
引用
收藏
页码:3308 / 3324
页数:17
相关论文
共 51 条
[1]   BENZOYL CYANIDE AS A SELECTIVE ACYLATING AGENT [J].
ABBAS, SA ;
HAINES, AH .
CARBOHYDRATE RESEARCH, 1975, 39 (02) :358-363
[2]   Metal catalyzed diazo transfer for the synthesis of azides from amines [J].
Alper, PB ;
Hung, SC ;
Wong, CH .
TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032
[3]   A molecular dynamics description of the conformational flexibility of the L-iduronate ring in glycosaminoglycans [J].
Angulo, J ;
Nieto, PM ;
Martín-Lomas, M .
CHEMICAL COMMUNICATIONS, 2003, (13) :1512-1513
[4]  
ANGULO J, UNPUB CHEM BIO CHEM
[5]  
Baumhof P, 2001, ANGEW CHEM INT EDIT, V40, P3672, DOI 10.1002/1521-3773(20011001)40:19<3672::AID-ANIE3672>3.0.CO
[6]  
2-Y
[7]  
Capila I, 2002, ANGEW CHEM INT EDIT, V41, P391
[8]   Structure and biological interactions of heparin and heparan sulfate [J].
Casu, B ;
Lindahl, U .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 57, 2001, 57 :159-206
[9]  
de la Paz ML, 2002, EUR J ORG CHEM, V2002, P840
[10]  
de Paz JL, 2001, CHEMBIOCHEM, V2, P673, DOI 10.1002/1439-7633(20010903)2:9<673::AID-CBIC673>3.0.CO