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

Werkhoven, P. R., van de Langemheen, H., van der Wal, S., Kruijtzer, J. A. W. and Liskamp, R. M.J. (2014) 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, 20(4), pp. 235-239. (doi:10.1002/psc.2624) (PMID:24599619)

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Abstract

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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Werkhoven, P. R., van de Langemheen, H., van der Wal, S., Kruijtzer, J. A. W., and Liskamp, R. M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Peptide Science
Publisher:John Wiley & Sons Ltd.
ISSN:1075-2617
ISSN (Online):1099-1387

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