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
收藏
页码：76 / 85
页数：10
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