Efficient reagent-saving method for the N-terminal labeling of bioactive peptides with organometallic carboxylic acids by solid-phase synthesis

Jack C. Slootweg, Bauke Albada, Daniel Siegmund, Nils Metzler-Nolte*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

10 Citations (Scopus)

Abstract

Labeling 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.
Original languageEnglish
Pages (from-to)3192-3196
JournalOrganometallics
Volume35
Issue number18
DOIs
Publication statusPublished - 2016

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