Synthesis of a C3-symmetric (1→6)-N-acetyl-β-D-glucosamine octadecasaccharide using click chemistry

被引:41
作者
Chen, Q [1 ]
Yang, F [1 ]
Du, YG [1 ]
机构
[1] Chinese Acad Sci, Ecoenvironm Sci Res Ctr, State Key Lab Environm Chem & Ecotoxicol, Beijing 100085, Peoples R China
基金
中国国家自然科学基金;
关键词
glycosylation; click chemistry; glucosamine; antitumor activity; thioglycosides;
D O I
10.1016/j.carres.2005.08.013
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
A C-3-symmetric (1-->6)-N-acetyl-beta-D-glucosamine octadecasaccharide was convergently synthesized on the basis of a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of azide and alkyne. The target octadecasaccharide showed good antitumor activity against H22 in the preliminary mice tests. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2476 / 2482
页数:7
相关论文
共 32 条
[1]   Polymer-immobilized carbohydrate ligands: Versatile chemical tools for biochemistry and medical sciences [J].
Bovin, NV ;
Gabius, HJ .
CHEMICAL SOCIETY REVIEWS, 1995, 24 (06) :413-+
[2]  
CHIHARA G, 1969, Nature (London), V222, P687
[3]   One-pot synthesis of triazole-linked glycoconjugates [J].
Chittaboina, S ;
Xie, F ;
Wang, Q .
TETRAHEDRON LETTERS, 2005, 46 (13) :2331-2336
[4]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[5]   Synthesis of sugar arrays in microtiter plate [J].
Fazio, F ;
Bryan, MC ;
Blixt, O ;
Paulson, JC ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14397-14402
[6]  
GOEDO EJ, 1998, NATURE, V392, P30
[7]   Di-, tri-, and tetravalent dendritic galabiosides that inhibit hemagglutination by Streptococcus suis at nanomolar concentration [J].
Hansen, HC ;
Haataja, S ;
Finne, J ;
Magnusson, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (30) :6974-6979
[8]   Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands [J].
Kitov, PI ;
Sadowska, JM ;
Mulvey, G ;
Armstrong, GD ;
Ling, H ;
Pannu, NS ;
Read, RJ ;
Bundle, DR .
NATURE, 2000, 403 (6770) :669-672
[9]   Emerging themes in medicinal glycoscience [J].
Koeller, KM ;
Wong, CH .
NATURE BIOTECHNOLOGY, 2000, 18 (08) :835-841
[10]   A potent and highly selective inhibitor of human α-1,3-fucosyltransferase via click chemistry [J].
Lee, LV ;
Mitchell, ML ;
Huang, SJ ;
Fokin, VV ;
Sharpless, KB ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9588-9589