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Stepwise triple-click functionalization of synthetic peptides

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Abstract

The increasing popularity of peptides as promising molecular scaffolds for biomedical applications and as valuable biochemical probes makes new methods allowing for their modification highly desirable. We describe herein an optimized protocol based on a sequence of CuAAC click reactions and selective deprotection steps, which leads to an efficient multi-functionalization of synthetic peptides. The methodology has been successfully applied to the construction of defined heteroglycopeptides and fluorophore–quencher-containing probes for proteases. The developed chemistry thus represents an important addition to the available toolbox of methods enabling efficient postsynthetic modification of peptides. The commercial availability of numerous azide probes further greatly extends the application potential of the described methodology.

Graphical abstract: Stepwise triple-click functionalization of synthetic peptides

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Publication details

The article was received on 09 Jul 2018, accepted on 30 Jul 2018 and first published on 09 Aug 2018


Article type: Communication
DOI: 10.1039/C8OB01617H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Stepwise triple-click functionalization of synthetic peptides

    A. Kovalová, R. Pohl and M. Vrabel, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01617H

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