Issue 19, 2013
From the journal:

Chemical Communications

Site-selective three-component reaction for dual-functionalization of peptides†

Henrik K. Munch,‡a   Jakob E. Rasmussen,‡ab   Gina Popa,b   Jørn B. Christensena  and  Knud J. Jensen*a  

* Corresponding authors

a Department of Chemistry, Faculty of Science, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg, Denmark
E-mail: kjj@chem.ku.dk

b The Novo Nordisk Foundation Center for Protein Research, Faculty of Health Sciences, Blegdamsvej 3b, Copenhagen N, Denmark

Abstract

A site-selective dual-functionalization of peptides is presented, involving readily available maleimides as well as N-hydroxylamines. The modification proceeds through a three component 1,3-dipolar cycloaddition, forming a stable product. This was exemplified by the one-pot attachment of two molecular imaging moieties to a tumor binding cyclic peptide, and was extended to the conjugation of a DOTA chelator to a 12 kDa protein.

Graphical abstract: Site-selective three-component reaction for dual-functionalization of peptides

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Article information

DOI
https://doi.org/10.1039/C3CC38673B
Article type
Communication
Submitted
03 Dec 2012
Accepted
21 Jan 2013
First published
22 Jan 2013

Chem. Commun., 2013,49, 1936-1938

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Site-selective three-component reaction for dual-functionalization of peptides

H. K. Munch, J. E. Rasmussen, G. Popa, J. B. Christensen and K. J. Jensen, Chem. Commun., 2013, 49, 1936 DOI: 10.1039/C3CC38673B

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