Peptide-based multiepitopic vaccine platforms via click reactions

Mostra el registre complet Registre parcial de l'ítem

• dc.contributor.author Forner, Mar, 1980-
• dc.contributor.author Defaus, Sira
• dc.contributor.author Andreu Martínez, David
• dc.date.accessioned 2025-10-28T18:04:53Z
• dc.date.available 2025-10-28T18:04:53Z
• dc.date.issued 2020
• dc.date.updated 2025-10-28T18:04:53Z
• dc.description.abstract Multimeric antigen display and high overall valency are increasingly regarded as strategic goals for potent and broadly efficacious synthetic vaccines with potential market prospects. Herein, a modular and versatile approach to multifunctional peptide-based vaccine platforms at multimilligram scale in reasonable yields is reported. Preparation of chemoselectively modified peptide building blocks of medium-to-large size, conjugation of these subunits, and final assembly were achieved by a combination of Michael-type thiol-ene addition and copper(I)-mediated alkyne-azide cycloaddition. The size and structural complexity of the building blocks required exploration of a further level of orthogonality, namely furan/maleimide Diels-Alder chemistry. After process optimization, a finely tuned, stepwise click approach has emerged as a workable, on-demand strategy to create macromolecular therapeutic vaccine assemblies.
• dc.description.sponsorship The study was supported by the Spanish Ministry of Economy and Competitiveness (MINECO) grants AGL2013-48923-C2 and AGL2017-84097-C2-2-R (to D.A.) as well as the MINECO "María de Maeztu" Program for Units of Excellence in R&D.
• dc.format.mimetype application/pdf
• dc.identifier.citation Forner M, Defaus S, Andreu D. Peptide-based multiepitopic vaccine platforms via click reactions. J Org Chem. 2020 Feb 7;85(3):1626-34. DOI: 10.1021/acs.joc.9b02798
• dc.identifier.doi http://dx.doi.org/10.1021/acs.joc.9b02798
• dc.identifier.issn 0022-3263
• dc.identifier.uri http://hdl.handle.net/10230/71682
• dc.language.iso eng
• dc.publisher American Chemical Society (ACS)
• dc.relation.ispartof The Journal of organic chemistry. 2020;85(3):1626-34
• dc.relation.projectID info:eu-repo/grantAgreement/ES/1PE/AGL2013-48923-C2
• dc.relation.projectID info:eu-repo/grantAgreement/ES/2PE/AGL2017-84097-C2-2-R
• dc.rights This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.9b02798.
• dc.rights.accessRights info:eu-repo/semantics/openAccess
• dc.subject.keyword Chemical reactions
• dc.subject.keyword High-performance liquid chromatography
• dc.subject.keyword Monomers
• dc.subject.keyword Peptides and proteins
• dc.subject.keyword Phosphates
• dc.title Peptide-based multiepitopic vaccine platforms via click reactions
• dc.type info:eu-repo/semantics/article
• dc.type.version info:eu-repo/semantics/acceptedVersion