Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides

被引：16
作者：
Del Bino, Linda [1 ]
Calloni, Ilaria [2 ]
Oldrini, Davide [1 ]
Raso, Maria Michelina [1 ]
Cuffaro, Rossella [1 ]
Arda, Ana [2 ]
Codee, Jeroen D. C. [3 ]
Jimenez-Barbero, Jesus [2 ,4 ,5 ]
Adamo, Roberto [1 ]
机构：
[1] GSK, Via Fiorentina 1, I-53100 Siena, Italy
[2] CIC BioGUNE, Bizkaia Technol Pk, Bldg 800, Derio 48160, Spain
[3] Leiden Univ, Dept Bioorgan Synth, NL-2333 Leiden, Netherlands
[4] Basque Fdn Sci IKERBASQUE, Bilbao 8009, Spain
[5] Univ Basque Country, Fac Sci & Technol, Dept Organ Chem 2, Leioa 48940, Spain
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 71期
基金：
欧盟地平线“2020”;
关键词：
carbohydrates; conformation analysis; glycosylation; regioselectivity; therapeutics; VACCINE;
D O I：
10.1002/chem.201903527
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Group B Streptococcus serotypes Ia and Ib capsular polysaccharides are key targets for vaccine development. In spite of their immunospecifity these polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and differ only in the connection of the Neu5Ac alpha 2-3Gal side chain to the GlcNAc unit, which is a beta 1-4 linkage in serotype Ia and a beta 1-3 linkage in serotype Ib. The development of efficient regioselective routes for GlcNAc beta 1-3[Glc beta 1-4]Gal synthons is described, which give access to different group B Streptococcus (GBS) Ia and Ib repeating unit frameshifts. These glycans were used to probe the conformation and molecular dynamics of the two polysaccharides, highlighting the different presentation of the protruding Neu5Ac alpha 2-3Gal moieties on the polysaccharide backbones and a higher flexibility of Ib polymer relative to Ia, which can impact epitope exposure.
引用
收藏
页码：16277 / 16287
页数：11
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