Sonogashira and “Click” reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)3(tpm)]+-based CO releasing molecules (tpm = tris(pyrazolyl)methane)

Hendrik Pfeiffer; Alfonso Rojas; Johanna Niesel; Ulrich Schatzschneider

doi:10.1039/B819091G

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Sonogashira and “Click” reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)₃(tpm)]⁺-based CO releasing molecules (tpm = tris(pyrazolyl)methane)†

Hendrik Pfeiffer,^a Alfonso Rojas,^a Johanna Niesel^a and Ulrich Schatzschneider*^a

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* Corresponding authors

^a Lehrstuhl für Anorganische Chemie I - Bioanorganische Chemie, Ruhr-Universität Bochum NC 3/74, Universitätsstr. 150, Bochum, Germany
E-mail: ulrich.schatzschneider@rub.de
Fax: +(49) 234 32–14378

Abstract

A recently identified photoactivatable CO releasing molecule (CORM) based on [Mn(CO)₃(tpm)]⁺ was conjugated to functionalized amino acids and model peptides using the Pd-catalyzed Sonogashira cross-coupling and the alkyne–azide 1,3-dipolar cycloaddition (“Click reaction”). Both were found to be fully compatible with all functional groups present. The CORM–peptide conjugates were isolated in reasonable yield and high purity, as indicated by IR spectroscopy, ESI mass spectrometry and RP-HPLC. The myoglobin assay was used to demonstrate that they have CO release properties identical those of the parent compound. This work thus opens the way for a targeted delivery of CORMs to cellular systems.

This article is part of the themed collection: Bioorganometallic chemistry

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Supplementary files

Synthesis of ligand precursors, additional HPLC traces, IRand mass spectra of the peptide conjugates PDF (417K)

Article information

DOI: https://doi.org/10.1039/B819091G
Article type: Paper
Submitted: 28 Oct 2008
Accepted: 04 Dec 2008
First published: 28 Jan 2009

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Dalton Trans., 2009, 4292-4298

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Sonogashira and “Click” reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)₃(tpm)]⁺-based CO releasing molecules (tpm = tris(pyrazolyl)methane)

H. Pfeiffer, A. Rojas, J. Niesel and U. Schatzschneider, Dalton Trans., 2009, 4292 DOI: 10.1039/B819091G

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Dalton Transactions