The application of 2,2,2-trichloroethyl sulfate to the synthesis of chondroitin sulfate C and D

被引：9

作者：

Matsushita, Kenya ^{[1
]}

Nakata, Tomomi ^{[2
]}

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

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：

CARBOHYDRATE RESEARCH | 2015年 / 406卷

关键词：

Protected sulfate; Sulfated oligosaccharide; Glycan synthesis;

D O I：

10.1016/j.carres.2015.01.007

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：

Chondroitin sulfates (CSs) have characteristic bioactivities that depend on sulfation patterns. Chemically synthesized CS oligosaccharides are valuable tools for elucidating the relationship between structures and bioactivities. 2,2,2-Trichloroethyl (TCE) sulfated sugars are highly soluble in nonpolar solvents, which is useful for the synthesis of sulfated oligosaccharides. We herein synthesized CS-C[beta GalNAc6S(1-4)beta GlcA] (1) and CS-D [beta GalNAc6S(1-4)beta GlcA2S] (2) disaccharides that possessed sulfate groups by TCE sulfation at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We revealed the superior functionalities of TCE sulfates during the synthesis of CS-C and -D, despite the unwanted side reactions in the acetamido-containing substrate. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：76 / 85

页数：10

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