om6b00544_si_001.cif (1.43 MB)
Efficient Reagent-Saving Method for the N‑Terminal Labeling of Bioactive Peptides with Organometallic Carboxylic Acids by Solid-Phase Synthesis
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posted on 2016-09-16, 12:09 authored by Jack C. Slootweg, H. Bauke Albada, Daniel Siegmund, Nils Metzler-NolteLabeling
of biomolecules with organometallic moieties holds great
promise as a tool for chemical biology and for the investigation of
biochemical signaling pathways. Herein, we report a robust and reproducible
synthetic strategy for the synthesis of ruthenocenecarboxylic acid,
giving the acid in 53% overall yield. This organometallic label was
conjugated via solid-phase peptide synthesis in near-quantitative
yield to a number of different biologically active peptides, using
only 1 equiv of the acid and coupling reagents, thereby avoiding wasting
the precious organometallic acid. This optimized method of stoichiometric
N-terminal acylation was then also successfully applied to conjugating
ferrocenecarboxylic acid and a novel organometallic ReI(CO)3 complex, showing the generality of the synthetic
procedure.
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Solid-Phase SynthesisOrganometallic Carboxylic AcidsCOorganometallic moietiesoptimized methodferrocenecarboxylic acidorganometallic acidnovel organometallic ReEfficient Reagent-Saving Methodruthenocenecarboxylic acidorganometallic labelstoichiometric N-terminal acylation1 equivBioactive Peptidessolid-phase peptide synthesischemical biology
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