Peptides conjugated to 2-alkoxy-8-oxo-adenine as potential synthetic vaccines triggering TLR7

Geoffroy P.P. Gential, Tim P. Hogervorst, Elena Tondini, Michel J. van de Graaff, Herman S. Overkleeft, Jeroen D.C. Codée, Gijsbert A. van der Marel, Ferry Ossendorp, Dmitri V. Filippov

Research output: Contribution to journalArticleAcademicpeer-review


Covalent linking of immunogenic oligopeptides with synthetic Toll-like receptor ligands is a useful approach to develop self-adjuvanting vaccines. In particular, small-molecule based agonists of Toll-like receptor 7 (TLR7) that are derived from 8-oxo-adenine core are potentially promising because these chemically robust TLR7 ligands can be connected to peptide T-cell epitopes via straightforward solid-phase peptide synthesis. In this contribution we present the synthesis of a Boc-protected 9-benzyl-2-alkoxy-8-oxo-adenine building block and its application in the online solid phase synthesis of three peptide conjugates that differ in the position of the TLR7 ligand within the peptide. The conjugates are able to induce dendritic cell maturation and T cell proliferation while the position of the ligand impacts T cell proliferation potency.
Original languageEnglish
Pages (from-to)1340-1344
JournalBioorganic & Medicinal Chemistry Letters
Issue number11
Publication statusPublished - Mar 2019
Externally publishedYes


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