Marco Körner, PhD, Postdoctoral Fellow at University of Iceland will present the above titled seminar on a topic from his thesis research at Eduard-Zintl-Institute for Inorganic and Physical Chemistry, Technische Universität Darmstadt.
In various chemical reactions, terminal alkynes serve as a starting material to generate more sophisticated structures. Since alkynes are highly energetic species, they are often referred to as “spring-loaded” reactants. Thus, alkynes provide access to a manifold of well-known reactions ranging from the acetylene-based chemistry described by Walter Reppe in the first half of the 20th century to reactions as 1,3-dipolar cycloadditions, catalytic hydrogenation, Sonogashira-type crosscoupling and application in Grignard reactions. During the last decade, the area of so-called “click chemistry” has experienced an enormous growth, whereas the copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) is without any doubt one of the most renowned specimens of this reaction class.
Whereas many examples of CuAAC reaction have been reported on amino acid side-chains in peptidic systems, this talk describes the application both of the CuAAC and its RuAAC-counterpart to install rigid amide-mimics within the peptide backbone.
Aside from azide-alkyne cycloaddition (AAC) applications, this talk further addresses the use of an alkyne-comprising amino acid in synthetic oligopeptides for studies via “parahydrogen-induced polarization” (PHIP). Since this approach employs para-enriched hydrogen as a spin-label in NMR spectroscopy targeting unsaturated substrate moieties, the molecular “toolbox” which is already established for AAC may as well provide an access to molecules for the applications of PHIP to almost the same extent.