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)?

Dalton Transactions Pub Date: 2009-01-28 DOI: 10.1039/B819091G

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.

Graphical abstract: 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)
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