Versatile convergent synthesis of a three peptide loop containing protein mimic of whooping cough pertactin by successive Cu(I)-catalyzed azide alkyne cycloaddition on an orthogonal alkyne functionalized TAC-scaffold

Journal of Peptide Science : an Official Publication of the European Peptide Society
P R WerkhovenRob M J Liskamp


Synthetic mimics of discontinuous epitopes may have a wide range of potential applications, including synthetic vaccines and inhibition of protein-protein interactions. However, synthetic access to these relatively complex peptide molecular constructs is limited. This paper describes a versatile convergent strategy for the construction of protein mimics presenting three different cyclic peptides. Using an orthogonal alkyne protection strategy, peptide loops were introduced successively onto a triazacyclophane scaffold via Cu(I)-catalyzed azide alkyne cycloaddition. This method provides rapid access to protein mimics requiring different peptide segments for their interaction and activity.


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Related Concepts

Bordetella pertussis outer membrane protein P69
Outer Membrane Lipoproteins, Bacterial
Bordetella pertussis Bacterium
Cyclic Peptides
Agglutinogen 2, Bordetella Pertussis
Molecular Mimicry
Spectrometry, Mass, Electrospray Ionization

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