SIOC OpenIR  > 生命有机化学国家重点实验室
Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase
Alternative Title作为肝素酶底物的肝素3-4糖寡糖库的建立
Xu P(徐鹏); Xu WZ(许伟长); Dai YW(代元伟); Yang Y(杨友); Yu B(俞飚)
2014
Source PublicationOrg. Chem. Front.
Volume1Pages:405-414
AbstractThe glycosylation reaction for construction of the challenging α-GlcN–(1→4)-GlcA/IdoA linkages has been investigated carefully. A standard protocol was thus fixed that employed 2-azido-glucopyranosyl N-phenyl trifluoroacetimidates as donors, TMSOTf as a catalyst, toluene as a solvent, and -30 °C as the working temperature. With this protocol, a variety of mono- and disaccharide donors and acceptors were condensed reliably to provide the corresponding coupled tri- and tetrasaccharides in satisfactory yields and α-selectivity, whereas a remote protecting group or a sugar unit in either the donor or the acceptor did affect considerably the outcome. The resulting tri- and tetrasaccharides bearing orthogonal protecting groups were then converted efficiently into the corresponding heparin tri- and tetrasaccharides via a robust approach involving saponification, O-sulfation, azide reduction, N-sulfation/N-acetylation, and global debenzylation. These heparin tri- and tetrasaccharides are structurally relevant to ΔHexA(2S)–GlcN(NS,6S)–GlcA–GlcN(NS,6S), a reported substrate of heparanase, and therefore could be exploited to examine the substrate specificity of this important enzyme.
Subject Area生命有机化学
DOI10.1039/c4qo00039k
URL查看原文
Language英语
Citation statistics
Cited Times:14[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38934
Collection生命有机化学国家重点实验室
Corresponding AuthorYu B(俞飚)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
Xu P,Xu WZ,Dai YW,et al. Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase[J]. Org. Chem. Front.,2014,1:405-414.
APA 徐鹏,许伟长,代元伟,杨友,&俞飚.(2014).Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase.Org. Chem. Front.,1,405-414.
MLA 徐鹏,et al."Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase".Org. Chem. Front. 1(2014):405-414.
Files in This Item:
File Name/Size DocType Version Access License
2014101.pdf(2966KB)期刊论文作者接受稿开放获取CC BY-NC-SAApplication Full Text
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[徐鹏]'s Articles
[许伟长]'s Articles
[代元伟]'s Articles
Baidu academic
Similar articles in Baidu academic
[徐鹏]'s Articles
[许伟长]'s Articles
[代元伟]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[徐鹏]'s Articles
[许伟长]'s Articles
[代元伟]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.