Issue 3, 2016

Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative “click” strategies

Abstract

The insertion of metal complexes in biologically active systems is of great interest in view of diagnostic and therapeutic applications as well as a precious tool to unveil biological mechanisms. Optimization of safe and biocompatible reactions is critical to achieve high functionalization efficiency. Herein we present the application of two modified versions of copper-catalyzed azide–alkyne cycloaddition (click) chemistry, namely a one-pot diazotransfer + azide–alkyne cycloaddition (one-pot click) and a copper-free photoactivated tetrazole–alkene cycloaddition (photoclick), for derivatization of peptides and peptide nucleic acids (PNAs) with ferrocene and cymantrene moieties. These metal fragments were chosen for their possible exploitation as redox and IR probes. We could demonstrate that one-pot click enables for efficient functionalization of propargyl-glycine and an alkyne-containing peptide with an amino-containing cymantrene precursor. In addition, we could show that photoclick allows for the insertion of maleimido-ferrocene into a peptide and a PNA sequence containing a tetrazole moiety.

Graphical abstract: Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative “click” strategies

Supplementary files

Article information

Article type
Research Article
Submitted
01 dek 2015
Accepted
06 yan 2016
First published
08 yan 2016
This article is Open Access
Creative Commons BY license

Inorg. Chem. Front., 2016,3, 397-405

Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative “click” strategies

C. Mari, S. Mosberger, N. Llorente, S. Spreckelmeyer and G. Gasser, Inorg. Chem. Front., 2016, 3, 397 DOI: 10.1039/C5QI00270B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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