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Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors
Wang, Zhen; Zhou, Luyuan; El-Boubbou, Kheireddine; Ye, Xin-Span; Huang, Xuefei
刊名JOURNAL OF ORGANIC CHEMISTRY
2007-08-17
DOI10.1021/jo070585g
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
引用统计
被引频次:101[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/64642
专题北京大学药学院
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
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GB/T 7714
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.
APA Wang, Zhen,Zhou, Luyuan,El-Boubbou, Kheireddine,Ye, Xin-Span,&Huang, Xuefei.(2007).Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors.JOURNAL OF ORGANIC CHEMISTRY,72(17),6409-6420.
MLA Wang, Zhen,et al."Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors".JOURNAL OF ORGANIC CHEMISTRY 72.17(2007):6409-6420.
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