Cu(I)-catalysed N–H insertion in water: a new tool for chemical biology

Tishinov, Kiril and Fei, Na and Gillingham, Dennis. (2013) Cu(I)-catalysed N–H insertion in water: a new tool for chemical biology. Chemical Science, 4 (12). pp. 4401-4406.

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Official URL: http://edoc.unibas.ch/dok/A6223562

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We demonstrate for the first time that Cu(I)-catalysis can deliver N–H insertion (NHI) with α-diazocarbonyl compounds in aqueous media. Despite being carried out in water only trace amounts of O–H insertion are seen, indicating the catalyst's overwhelming preference for NHI. Our optimized conditions for NHI converged with those used for the Cu-catalyzed azide–alkyne cycloaddition (CuAAC) for bioconjugation, spurring us to develop an auto-tandem catalytic process where both catalytic cycles operate simultaneously in one-pot. We explore the scope of the method with both small molecule and complex DNA and RNA substrates.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Gillingham)
UniBasel Contributors:Gillingham, Dennis
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:17 Mar 2017 13:36
Deposited On:27 Feb 2014 15:46

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