title: Synthesis and affinities of C3-symmetric thioglycoside-containing trimannosides.
abstract: Thioglycoside-containing trimannose analogs were designed and prepared to mimic the natural N-glycan core trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man. (1→6)-S-Linked trimannoside 1 and its trivalent cluster 2 were synthesized in 11 and 15 steps, respectively, taking advantages of the armed mannopyranosyl trichloroacetimidate as glycosyl donor. Hemagglutination inhibition of the two new thiomannotriose analogs was preliminarily examined. Comparing to the parent trimannoside α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man-OMe, the cluster mannotrioside 2 presented a comparable binding affinity to Con A, while the monomer 6-S-trimannoside 1 exhibited a slightly lower inhibition ability.
authors.affiliation: State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Jingjing
authors.initials: J
authors.lastname: Bi
authors.affiliation: State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Chuanfang
authors.initials: C
authors.lastname: Zhao
authors.affiliation: School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Cui
authors.affiliation: State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Chaoli
authors.initials: C
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Qiuli
authors.initials: Q
authors.lastname: Shan
authors.affiliation: State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China; National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, Jiangxi, China. Electronic address: duyuguo@rcees.ac.cn.
authors.forename: Yuguo
authors.initials: Y
authors.lastname: Du
mesh_terms: D003208:Concanavalin A / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D008362:Mannosides; D013865:Thioglycosides; D014312:Trisaccharides; D003208:Concanavalin A
keywords: Con A; Glucocluster; Hemagglutination; Mutivalent effect; Thiooligosaccharides