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Issue 9, 2018
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Multicomponent polysaccharide–protein bioconjugation in the development of antibacterial glycoconjugate vaccine candidates

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Abstract

A new synthetic strategy for the development of multivalent antibacterial glycoconjugate vaccines is described. The approach comprises the utilization of an isocyanide-based multicomponent process for the conjugation of functionalized capsular polysaccharides of S. pneumoniae and S. Typhi to carrier proteins such as diphtheria and tetanus toxoids. For the first time, oxo- and carboxylic acid-functionalized polysaccharides could be either independently or simultaneously conjugated to immunogenic proteins by means of the Ugi-multicomponent reaction, thus leading to mono- or multivalent unimolecular glycoconjugates as vaccine candidates. Despite the high molecular weight of the two or three reacting biomolecules, the multicomponent bioconjugation proved highly efficient and reproducible. The Ugi-derived glycoconjugates showed notable antigenicity and elicited good titers of functional specific antibodies. To our knowledge, this is the only bioconjugation method that enables the incorporation of two different polysaccharidic antigens to a carrier protein in a single step. Applications in the field of self-adjuvanting, eventually anticancer, multicomponent vaccines are foreseeable.

Graphical abstract: Multicomponent polysaccharide–protein bioconjugation in the development of antibacterial glycoconjugate vaccine candidates

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Supplementary files

Article information


Submitted
26 Dec 2017
Accepted
19 Jan 2018
First published
19 Jan 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 2581-2588
Article type
Edge Article

Multicomponent polysaccharide–protein bioconjugation in the development of antibacterial glycoconjugate vaccine candidates

Y. Méndez, J. Chang, A. R. Humpierre, A. Zanuy, R. Garrido, A. V. Vasco, J. Pedroso, D. Santana, L. M. Rodríguez, D. García-Rivera, Y. Valdés, V. Vérez-Bencomo and D. G. Rivera, Chem. Sci., 2018, 9, 2581
DOI: 10.1039/C7SC05467J

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