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A Highly alpha-Stereoselective Synthesis of Oligosaccharide Fragments of the Vi Antigen from Salmonella typhi and Their Antigenic Activities
Yang, Lin1; Zhu, Jingjing1,2; Zheng, Xiu-Jing1; Tai, Guihua2; Ye, Xin-Shan1
关键词Antigens Glycosylation Oxazolidinones Salmonella Typhi Stereoselectivity Vi Antigens
刊名CHEMISTRY-A EUROPEAN JOURNAL
2011-12-01
DOI10.1002/chem.201102615
17期:51页:14518-14526
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Multidisciplinary
研究领域[WOS]Chemistry
关键词[WOS]CAPSULAR POLYSACCHARIDE VACCINE ; PRE-ACTIVATION PROTOCOL ; DEHYDRATIVE GLYCOSYLATION ; FEVER ; GLUCOSAMINE ; DERIVATIVES ; CHILDREN ; THIOGLYCOSIDES ; PHAGOCYTOSIS ; REACTIVITY
英文摘要

In this paper, a convenient approach to the synthesis of the repeating alpha-(1 -> 4)-linked N-acetyl galactosaminuronic acid units from the capsular polysaccharide of Salmonella typhi is reported. The exclusively alpha-stereoselective glycosylation reactions were achieved by using oxazolidinone-protected glycosides as building blocks based on a pre-activation protocol. Di-, tri-, and tetrasaccharides were prepared by this short and efficient approach in high yields. The enzyme-linked immunosorbent assay experiments show that our synthetic tri- and tetrasaccharide had much higher antigenic activities than previously reported ones in the inhibition of antibody binding by the native polysaccharide. The results demonstrate that the antigenic activities of saccharides can be strengthened greatly by increasing the number of acetyl groups present.

语种英语
WOS记录号WOS:000298542300023
项目编号20732001
资助机构National Natural Science Foundation of China
引用统计
被引频次:16[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/400002259/57036
专题北京大学药学院
北京大学药学院_天然药物与仿生药物国家重点实验室
北京大学药学院_药物化学系
北京大学第二临床医学院_图书馆
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat A0nd Biomimet Drugs, Beijing 100191, Peoples R China
2.NE Normal Univ, Sch Life Sci, Changchun 130024, Peoples R China
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GB/T 7714
Yang, Lin,Zhu, Jingjing,Zheng, Xiu-Jing,et al. A Highly alpha-Stereoselective Synthesis of Oligosaccharide Fragments of the Vi Antigen from Salmonella typhi and Their Antigenic Activities[J]. CHEMISTRY-A EUROPEAN JOURNAL,2011,17(51):14518-14526.
APA Yang, Lin,Zhu, Jingjing,Zheng, Xiu-Jing,Tai, Guihua,&Ye, Xin-Shan.(2011).A Highly alpha-Stereoselective Synthesis of Oligosaccharide Fragments of the Vi Antigen from Salmonella typhi and Their Antigenic Activities.CHEMISTRY-A EUROPEAN JOURNAL,17(51),14518-14526.
MLA Yang, Lin,et al."A Highly alpha-Stereoselective Synthesis of Oligosaccharide Fragments of the Vi Antigen from Salmonella typhi and Their Antigenic Activities".CHEMISTRY-A EUROPEAN JOURNAL 17.51(2011):14518-14526.
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