北京大学医学部机构知识库
Advanced  
IR@PKUHSC  > 北京大学药学院  > 期刊论文
学科主题: 药学
题名:
Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors
作者: Wang, Zhen; Zhou, Luyuan; El-Boubbou, Kheireddine; Ye, Xin-Span; Huang, Xuefei
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2007-08-17
DOI: 10.1021/jo070585g
卷: 72, 期:17, 页:6409-6420
收录类别: SCI ; IC ; CCR
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: STEREOSELECTIVE GLYCOSYLATION ; OLIGOSACCHARIDE SYNTHESIS ; YTTERBIUM(III) TRIFLATE ; CHEMICAL-SYNTHESIS ; CANCER ; TRISACCHARIDE ; TETRASACCHARIDE ; HEXOPYRANOSES ; ACTIVATION ; GLYCOSIDES
英文摘要:

Two efficient routes for the rapid assembly of the tumor-associated carbohydrate antigen Globo-H hexasaccharide 2 by a preactivation based iterative one-pot strategy are reported. The first method involves the sequential coupling of four glycosyl building blocks, leading to the desired hexasaccharide in 47% overall yield in one-pot synthesis. Although model studies on constructing the challenging Gal-alpha-(14)-Gal linkage in Gb3 trisaccharide yielded the desired a linkage almost exclusively, a similar approach to assemble the hexasaccharide led to the formation of a significant amount of beta anomer. As an alternative, the second synthesis utilized three components in one pot with the Gal-alpha-(1-4)-Gal linkage preformed, producing the desired hexasaccharide in a similar overall yield as the four component approach. Both methods demonstrate that oligosaccharides containing a and a linkages within the same molecule can be constructed in one pot via a preactivation based approach with higher glyco-assembly efficiencies than the automated solid-phase synthesis strategy. Furthermore, because glycosylations can be carried out independent of anomeric reactivities of donors, it is not necessary to differentiate anomeric reactivities of building blocks through extensive protective group adjustment for chemoselective glycosylation. This confers great flexibilities in the building block design, allowing matching of the donor with the acceptor, leading to improved overall yield.

语种: 英语
WOS记录号: WOS:000248793400009
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/64642
Appears in Collections:北京大学药学院_期刊论文

Files in This Item:

There are no files associated with this item.


作者单位: 1.Univ Toledo, Dept Chem, Toledo, OH 43606 USA
2.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China

Recommended Citation:
Wang, Zhen,Zhou, Luyuan,El-Boubbou, Kheireddine,et al. Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors[J]. JOURNAL OF ORGANIC CHEMISTRY,2007,72(17):6409-6420.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[Wang, Zhen]'s Articles
[Zhou, Luyuan]'s Articles
[El-Boubbou, Kheireddine]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[Wang, Zhen]‘s Articles
[Zhou, Luyuan]‘s Articles
[El-Boubbou, Kheireddine]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit

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

 

 

Valid XHTML 1.0!
Copyright © 2007-2017  北京大学医学部 - Feedback
Powered by CSpace