Issue 20, 2009
From the journal:

Organic & Biomolecular Chemistry

Application of copper(i) catalyzed azide–alkyne[3+2] cycloaddition to the synthesis of template-assembled multivalent peptide conjugates†

Olga Avrutina,‡a   Martin Empting,‡a   Sebastian Fabritz,a   Matin Daneschdar,a   Holm Frauendorf,b   Ulf Diederichsenb  and  Harald Kolmar*a  

* Corresponding authors

a Clemens-Schöpf Institute of Organic Chemistry and Biochemistry, Darmstadt University of Technology, Petersenstr. 22, Darmstadt, Germany

b Institut für Organische und Biomolekulare Chemie, Georg-August Universität Göttingen, Tamannstraße 2, Göttingen, Germany

Abstract

Here we describe the facile generation of tetravalent peptide conjugates via a copper(I) catalyzed azide–alkyne cycloaddition (CuAAC) using a cyclic peptide template as a versatile conjugation scaffold. This stable and rigid framework is a conformationally constrained cyclic β-sheet decorated with spatially defined alkyne moieties that serve as selectively addressable coupling sites. The proposed method allows for the effective coupling of unprotected peptide monomers in water at room temperature within comparatively short reaction times. The resulting conjugates display the ligands in an oriented manner, thus allowing for multivalent interactions with given target molecules, which may contribute to enhanced affinity and specificity. In addition, the selected scaffold offers an orthogonal coupling site for the incorporation of fluorescent labels or radioligands.

Graphical abstract: Application of copper(i) catalyzed azide–alkyne [3+2] cycloaddition to the synthesis of template-assembled multivalent peptide conjugates

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Article information

DOI
https://doi.org/10.1039/B908261A
Article type
Paper
Submitted
27 Apr 2009
Accepted
02 Jul 2009
First published
25 Aug 2009

Org. Biomol. Chem., 2009,7, 4177-4185

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Application of copper(I) catalyzed azide–alkyne [3+2] cycloaddition to the synthesis of template-assembled multivalent peptide conjugates

O. Avrutina, M. Empting, S. Fabritz, M. Daneschdar, H. Frauendorf, U. Diederichsen and H. Kolmar, Org. Biomol. Chem., 2009, 7, 4177 DOI: 10.1039/B908261A

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