Concise synthesis of sialic acid containing hexasaccharide corresponding to group B Streptococcus type IX capsular polysaccharide

被引：2
作者：
Sahaji, Samim [1 ]
Manna, Tapasi [1 ]
Misra, Anup Kumar [1 ]
机构：
[1] Bose Inst, Dept Chem Sci, Block EN-80,Sect 5, Kolkata 700091, India
来源：
TETRAHEDRON | 2023年 / 141卷
关键词：
Carbohydrates; Hexasaccharide; Polysaccharide; Glycosylation; Glycoside; Streptococcus; NEISSERIA-MENINGITIDIS SEROGROUP; CHEMICAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HIGHLY EFFICIENT; REPEATING UNIT; O-SIALYLATION; GLYCOSYLATION; COLONIZATION; HCLO4-SIO2; OLIGOSACCHARIDES;
D O I：
10.1016/j.tet.2023.133499
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient block [3 + 2+1] glycosylation strategy has been developed for the synthesis of sialic acid containing hexasaccharide repeating unit having a 2-aminoethyl linker at the reducing end corresponding to the capsular polysaccharide of Group B Streptococcus type IX strain. A disaccharide thioglycoside has been prepared applying "orthogonal latent-active" glycosylation of a thioglycoside acceptor with a thioglycoside donor. A specially designed sialic acid thioglycoside donor has been used to furnish a-glycosidic linkage. Thioglycosides were used as glycosyl donors throughout the synthetic strategy. A combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4eSiO2), a solid acid substitute, was used as a thiophilic promoter for the activation of thioglycosides.& COPY; 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数：7
相关论文
共 56 条
  • [1] Mild and efficient method for the cleavage of benzylidene acetals using HClO4-SiO2 and direct conversion of acetals to acetates
    Agnihotri, Geetanjali
    Misra, Anup Kumar
    [J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3653 - 3658
  • [2] Donor-Reactivity-Controlled Sialylation Reactions
    Asressu, Kesatebrhan Haile
    Chang, Chun-Wei
    Lam, Sarah
    Wang, Cheng-Chung
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (32) : 4525 - 4530
  • [3] Principles of modern solid-phase oligosaccharide synthesis
    Bennett, Clay S.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (11) : 1686 - 1698
  • [4] Structure of the Type IX Group B Streptococcus Capsular Polysaccharide and Its Evolutionary Relationship with Types V and VII
    Berti, Francesco
    Campisi, Edmondo
    Toniolo, Chiara
    Morelli, Laura
    Crotti, Stefano
    Rosini, Roberto
    Romano, Maria Rosaria
    Pinto, Vittoria
    Brogioni, Barbara
    Torricelli, Giulia
    Janulczyk, Robert
    Grandi, Guido
    Margarit, Immaculada
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2014, 289 (34) : 23437 - 23448
  • [5] Group B Streptococcus chimeric capsular polysaccharides as novel multivalent vaccine candidates
    Campisi, Edmondo
    Rosini, Roberto
    Romano, Maria Rosaria
    Balducci, Evita
    Pinto, Vittoria
    Brogioni, Barbara
    De Ricco, Riccardo
    Fabbrini, Monica
    Spagnuolo, Angela
    Chiarot, Emiliano
    Berti, Francesco
    Margarit, Immaculada
    [J]. GLYCOCONJUGATE JOURNAL, 2021, 38 (04) : 447 - 457
  • [6] Synthesis of Group B Streptococcus type III polysaccharide fragments for evaluation of their interactions with monoclonal antibodies
    Cattaneo, Vittorio
    Carboni, Filippo
    Oldrini, Davide
    De Ricco, Riccardo
    Donadio, Nunzio
    Margarit Y Ros, Immaculada
    Berti, Francesco
    Adamo, Roberto
    [J]. PURE AND APPLIED CHEMISTRY, 2017, 89 (07) : 855 - 875
  • [7] Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines
    Chakraborti, AK
    Gulhane, R
    [J]. CHEMICAL COMMUNICATIONS, 2003, (15) : 1896 - 1897
  • [8] HClO4-SiO2 as a new, highly efficient, inexpensive and reusable catalyst for N-tert-butoxycarbonylation of amines
    Chakraborti, Asit K.
    Chankeshwara, Sunay V.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (14) : 2769 - 2771
  • [9] Structural and genetic diversity of group B Streptococcus capsular polysaccharides
    Cieslewicz, MJ
    Chaffin, D
    Glusman, G
    Kasper, D
    Madan, A
    Rodrigues, S
    Fahey, J
    Wessels, MR
    Rubens, CE
    [J]. INFECTION AND IMMUNITY, 2005, 73 (05) : 3096 - 3103
  • [10] Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides
    Del Bino, Linda
    Calloni, Ilaria
    Oldrini, Davide
    Raso, Maria Michelina
    Cuffaro, Rossella
    Arda, Ana
    Codee, Jeroen D. C.
    Jimenez-Barbero, Jesus
    Adamo, Roberto
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (71) : 16277 - 16287
123456