Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative 'click' strategies
| Autor: | Sarah Spreckelmeyer, Cristina Mari, Sandro Mosberger, Nuria Llorente, Gilles Gasser |
|---|---|
| Přispěvatelé: | University of Zurich, Gasser, Gilles |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
10120 Department of Chemistry 010405 organic chemistry Chemistry 1604 Inorganic Chemistry Sequence (biology) Peptide 010402 general chemistry 01 natural sciences Combinatorial chemistry Cycloaddition 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Ferrocene 540 Chemistry Nucleic acid Surface modification Moiety Tetrazole |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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