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Convergent Synthesis of Glycodendropeptides by Click Chemistry Approaches

AuthorsKowalczyk, Wioleta; Mascaraque, Ainhoa ; Sánchez-Navarro, Macarena ; Rojo, Javier ; Andreu, David
Issue Date2012
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry 2012: 4565- 4573 (2012)
AbstractMannosylation facilitates the uptake of immunogenic peptides by antigen-processing cells expressing mannose receptors at their surface. Mannose-receptor interactions not only induce internalization but also trigger strong T-cell stimulation, such as that of the dendritic cell-specific intercellular ICAM-3 grabbing non-integrin (DC-SIGN), a lectin that plays a key role in the immune response against different pathogens. We describe here two efficient synthetic strategies for structurally well-defined mannose-displaying glyco- dendropeptides with up to 16 peptide and 9 mannose copies. Our approaches integrate previously optimized synthetic methods for producing both peptide and glycan dendrimers, and make extensive use of CuI-catalyzed Huisgen 1,3-dipolar cycloaddition for both the building of the glycodendron moieties and their subsequent conjugation to the peptide components. These strategies are versatile and straightforward enabling full control of chemical structure as well as readily tunable valency.
Identifiersdoi: 10.1002/ejoc.201200428
issn: 1434-193X
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