Header

UZH-Logo

Maintenance Infos

Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative “click” strategies


Mari, Cristina; Mosberger, Sandro; Llorente, Nuria; Spreckelmeyer, Sarah; Gasser, Gilles (2016). Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative “click” strategies. Inorganic Chemistry Frontiers, 3(3):397-405.

Abstract

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.

Abstract

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.

Statistics

Citations

Dimensions.ai Metrics
2 citations in Web of Science®
1 citation in Scopus®
1 citation in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

16 downloads since deposited on 09 Feb 2017
12 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:09 Feb 2017 14:25
Last Modified:02 Feb 2018 12:12
Publisher:Royal Society of Chemistry
ISSN:2052-1553
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/C5QI00270B

Download

Download PDF  'Insertion of organometallic moieties into peptides and peptide nucleic acids using alternative “click” strategies'.
Preview
Filetype: PDF
Size: 863kB
View at publisher
Licence: Creative Commons: Attribution 3.0 Unported (CC BY 3.0)