Synthesis of a conjugable hexasaccharide corresponding to the capsular polysaccharide of Campylobacter jejuni strain BH0142  

作　　者：Zijiao Hou Jianjun Wang Xinxin Zhang Peng Wang Ni Song Ming Li 

机构地区：[1]Molecular Synthesis Center,Key Laboratory of Marine Medicine,Chinese Ministry of Education,Shandong Key Laboratory of Glycoscience and Glycotechnology,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China [2]Laboratory for Marine Drugs and Bioproducts,Pilot National Laboratory for Marine Science and Technology,Qingdao 266237,China [3]Shandong Key Laboratory of Glycoscience and Glycotechnology,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China

出　　处：《Chinese Chemical Letters》2023年第5期209-212,共4页中国化学快报（英文版）

基　　金：financial support from the Marine S&T Fund of Shandong Province for Pilot National Laboratory for Marine Science and Technology(Qingdao)(No.2022QNLM030003-2);the National Natural Science Foundation of China(Nos.21977088 and 21672194);the National Natural Science Foundation of China-Shandong Joint Foundation(No.U1906213)。

摘　　要：The first assembly of a conjugation-ready hexasaccharide from the capsular glycan of C.jejuni.strain BH0142 has been accomplished.The synthesis features the efficient preparation of 6-deoxy-D-idoheptopyranosyl fluoride donors proceeding from allylα-D-C-glucopyranoside by a C1-to-C5 switch strategy with radical dehydroxymethylative fluorination as a key step,stereocontrolled construction of 1,2-trans-α-D-ido-heptopyranosidic bonds and of 1,2-cis-α-D-galactopyranosidic linkages.The obtained target oligosaccharide sets a solid foundation for making structurally-defined multivalent glycoconjugate vaccine candidates against C.jejuni.infections.

关 键 词：6-Deoxy-D-ido-heptopyranosyl fluoride Oligosaccharide synthesis Campylobacter jejuni BH0142 Capsular polysaccharide Dehydroxymethylative fluorination GLYCOSYLATION 

分 类 号：TQ460.1[化学工程—制药化工]