Efficient chemical synthesis of sialic acid related oligosaccharides

被引:2
作者
Zhao, C
Zhen, X
Zhang, H
Ding, Y [1 ]
机构
[1] Zhongshan Univ, Sch Chem & Chem Engn, Guangzhou, Peoples R China
[2] Yunnan Univ, Dept Chem, Yunnan, Peoples R China
关键词
D O I
10.2174/1570178054640732
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very efficient strategy for the chemical synthesis of the sialyl Lewis X tetrasaccharide is reported. Starting from four simple monosaccharide building blocks, sialyl Lewis X was obtained in seven steps. By using similar strategy, sialyl LacNAc and sulfated sialyl LacNAc trisaccharides were also synthesized.
引用
收藏
页码:521 / 523
页数:3
相关论文
共 16 条
[1]   Recent advances in O-sialylation [J].
Boons, GJ ;
Demchenko, AV .
CHEMICAL REVIEWS, 2000, 100 (12) :4539-+
[2]   An economical synthesis of Lewis X, sialyl Lewis X and their alpha-galactosyl analogues [J].
Dekany, G ;
Wright, K ;
Toth, I .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (07) :983-999
[3]   Efficient synthesis of 3′-glycosylated LacNAc-based oligosaccharides [J].
Ding, YL ;
Fukuda, M ;
Hindsgaul, O .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (14) :1903-1908
[4]   A high yielding chemical synthesis of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide; Examples of regio- and stereodifferentiated glycosylations [J].
Ellervik, U ;
Magnusson, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9314-9322
[5]  
FUKUSHIMA K, 1984, CANCER RES, V44, P5279
[6]   HIGH-AFFINITY BINDING OF THE LEUKOCYTE ADHESION MOLECULE L-SELECTIN TO 3'-SULFATED-LEA AND 3'-SULFATED-LEX OLIGOSACCHARIDES AND THE PREDOMINANCE OF SULFATE IN THIS INTERACTION DEMONSTRATED BY BINDING-STUDIES WITH A SERIES OF LIPID-LINKED OLIGOSACCHARIDES [J].
GREEN, PJ ;
TAMATANI, T ;
WATANABE, T ;
MIYASAKA, M ;
HASEGAWA, A ;
KISO, M ;
YUEN, CT ;
STOLL, MS ;
FEIZI, T .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 188 (01) :244-251
[7]   SYNTHESIS OF THE METHYL THIOGLYCOSIDES OF 4 STEREOISOMERS AND THE 2-METHOXY DERIVATIVE OF L-FUCOSE [J].
HASEGAWA, A ;
KATO, M ;
ANDO, T ;
ISHIDA, H ;
KISO, M .
CARBOHYDRATE RESEARCH, 1995, 274 :155-163
[8]   Selectin ligands: 2,3,4-Tri-O-acetyl-6-O-pivaloyl-alpha/beta-galactopyranosyl halide as novel glycosyl donor for the synthesis of 3-O-sialyl or 3-O-sulfo Le(x) and Le(a) type structures [J].
Jain, RK ;
Vig, R ;
Locke, RD ;
Mohammad, A ;
Matta, KL .
CHEMICAL COMMUNICATIONS, 1996, (01) :65-67
[9]   Generation of molecular diversity on N-acetyllactosamine via O-cyanomethyl ethers [J].
Malet, C ;
Hindsgaul, O .
CARBOHYDRATE RESEARCH, 1997, 303 (01) :51-65
[10]   STEREOSELECTIVE SYNTHESIS OF 2-THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID [J].
MARRA, A ;
SINAY, P .
CARBOHYDRATE RESEARCH, 1989, 187 (01) :35-42