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Issue 2, 2016
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Molecular construction of HIV-gp120 discontinuous epitope mimics by assembly of cyclic peptides on an orthogonal alkyne functionalized TAC-scaffold

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Abstract

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.

Graphical abstract: Molecular construction of HIV-gp120 discontinuous epitope mimics by assembly of cyclic peptides on an orthogonal alkyne functionalized TAC-scaffold

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Publication details

The article was received on 27 Sep 2015, accepted on 05 Nov 2015 and first published on 05 Nov 2015


Article type: Paper
DOI: 10.1039/C5OB02014J
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Citation: Org. Biomol. Chem., 2016,14, 701-710
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    Molecular construction of HIV-gp120 discontinuous epitope mimics by assembly of cyclic peptides on an orthogonal alkyne functionalized TAC-scaffold

    P. R. Werkhoven, M. Elwakiel, T. J. Meuleman, H. C. Quarles van Ufford, J. A. W. Kruijtzer and R. M. J. Liskamp, Org. Biomol. Chem., 2016, 14, 701
    DOI: 10.1039/C5OB02014J

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