Synthesis of β-D-GalNac(4,6-diS)(1-4)[α-L-Fuc(2,4-diS)(1-3)]-β-D-GlcA, a novel trisaccharide unit of chondroitin sulfate with a fucose branch

被引：26

作者：

Tamura, Jun-ichi ^{[1
,2
]}

Tanaka, Haruna ^{[2
]}

Nakamura, Ayumi ^{[2
]}

Takeda, Naoko ^{[1
]}

机构：

[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Tottori 6808552, Japan

[2] Tottori Univ, Fac Reg Sci, Dept Reg Environm, Tottori 6808551, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 30期

关键词：

Chondroitin sulfate; Glycosaminoglycan; Sea cucumber; Glycosylation; SEA-CUCUMBER; BODY-WALL; GLYCOSAMINOGLYCAN;

D O I：

10.1016/j.tetlet.2013.05.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel glycosaminoglycans isolated from the body wall of sea cucumbers consist of chondroitin sulfates like polysaccharides. We have synthesized a representative repeating trisaccharide composed of a chondroitin backbone having a fucose (Fuc) branch at O-3 of glucuronic acid (GlcA), beta-D-GalNac(4,6-diS)(1-4)[alpha-L-Fuc(2,4-diS)(1-3)]-beta-D-GlcA, in a stereocontrolled manner. Regiospecific sulfation at 04,6 and O-2,4 of the N-acetylgalactosamine (GalNAc) and Fuc residues, respectively, was successfully achieved. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3940 / 3943

页数：4

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