Molecular construction of HIV-gp120 discontinuous epitope mimics by assembly of cyclic peptides on an orthogonal alkyne functionalized TAC-scaffold
Autor: | Paul R. Werkhoven, H. C. Quarles van Ufford, T. J. Meuleman, Rob M. J. Liskamp, John A. W. Kruijtzer, M. Elwakiel |
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Jazyk: | angličtina |
Rok vydání: | 2016 |
Předmět: |
Models
Molecular Azides Scaffold Alkyne HIV Envelope Protein gp120 010402 general chemistry Peptides Cyclic 01 natural sciences Chemical synthesis Biochemistry Epitope Epitopes Structure-Activity Relationship chemistry.chemical_compound Structure–activity relationship Physical and Theoretical Chemistry chemistry.chemical_classification Vaccines Synthetic Cycloaddition Reaction Molecular Structure 010405 organic chemistry Organic Chemistry Combinatorial chemistry Cycloaddition Cyclic peptide 0104 chemical sciences Immobilized Proteins chemistry Alkynes CD4 Antigens Biophysics Azide |
Zdroj: | Organic & Biomolecular Chemistry, 14(2), 701. Royal Society of Chemistry |
ISSN: | 1477-0520 |
Popis: | Mimics of discontinuous epitopes of for example bacterial or viral proteins may have considerable potential for the development of synthetic vaccines, especially if conserved epitopes can be mimicked. However, due to the structural complexity and size of discontinuous epitopes molecular construction of these mimics remains challeging. We present here a convergent route for the assembly of discontinuous epitope mimics by successive azide alkyne cycloaddition on an orthogonal alkyne functionalized scaffold. Here the synthesis of mimics of the HIV gp120 discontinuous epitope that interacts with the CD4 receptor is described. The resulting protein mimics are capable of inhibition of the gp120-CD4 interaction. The route is convergent, robust and should be applicable to other discontinuous epitopes. |
Databáze: | OpenAIRE |
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