文献类型：期刊文献

英文题名：Total Synthesis of the Trisaccharide Antigen of the Campylobacter jejuni RM1221 Capsular Polysaccharide via de Novo Synthesis of the 6-Deoxy-D-manno-heptose Building Blocks

作者：Wang, Xiaoman[1];Chen, Yan[1];Wang, Junchang[1];Yang, You[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2019

卷号：84

期号：5

起止页码：2393

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20191006591185);WOS:【SCI-EXPANDED(收录号:WOS:000460491600002)】；

基金：Financial support from the National Thousand Young Talents Program (Y100-4Q-1701, YC0140103), the National Natural Science Foundation of China (21871081), and the Fundamental Research Funds for the Central Universities (22221818014) is gratefully acknowledged.

语种：英文

外文关键词：Condensation reactions - Stereoselectivity - Synthesis (chemical) - Catalysis - Bacteria - Ketones

摘要：A de novo approach utilizing the d-proline-catalyzed and LDA-promoted aldol reactions as key steps for the preparation of differentiated-protected 6-deoxy-d-manno-heptose building blocks was developed. PPh3AuBAr4F-catalyzed glycosylation with the 6-deoxy-d-manno-heptosyl o-hexynylbenzoate as donor was demonstrated as a direct and practical method for the stereoselective synthesis of the beta-linked 6-deoxy-d-manno-heptoside as the major product. Coupling of the 6-deoxy-a-d-manno-heptosyl H-phosphonate with the 3-hydroxyl disaccharide acceptor based on H-phosphonate chemistry was described for the construction of the trisaccharide skeleton with the acid-labile phosphodiester linkage. Finally, first total synthesis of the unique trisaccharide antigen of the capsular polysaccharide of Campylobacter jejuni RM1221 that belongs to HS:53 serotype complex was accomplished for further evaluation as vaccine candidate against C. jejuni RM1221 infection.