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      Carbonylation as a novel method for the assembly of pyrazine based oligoamide alpha-helix mimetics

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          Abstract

          Carbonylative assembly of pyrazine based oligoamide alpha-helix mimetics.

          Abstract

          The design and synthesis of oligoamide α-helix peptidomimetics is reported. The oligoamide type systems are prepared in a modular fashion by coupling the monomers using palladium-catalyzed carbonylation chemistry. This enabled us to use substrates with a low nucleophilicity, leading to previously unreported pyrazine based oligoamide α-helix mimetics. The proof of principle is given by synthesizing a small set of compounds. Various end-capping groups were introduced and also a mixed multimer was successfully prepared.

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          Most cited references44

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          Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds

          Anne Brennführer, Helfried Neumann, Matthias Beller (2009)
          Article 0 comments Cited 239 times – based on 0 reviews     Review now
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            Inhibition of α-helix-mediated protein-protein interactions using designed molecules.

            Jeffrey N. Murphy, Jonathan J. Wilson, Kérya Long … (2013)
            Inhibition of protein-protein interactions (PPIs) represents a significant challenge because it is unclear how they can be effectively and selectively targeted using small molecules. Achieving this goal is critical given the defining role of these interactions in biological processes. A rational approach to inhibitor design based on the secondary structure at the interface is the focus of much research, and different classes of designed ligands have emerged, some of which effectively and selectively disrupt targeted PPIs. This Review discusses the relevance of PPIs and, in particular, the importance of α-helix-mediated PPIs to chemical biology and drug discovery with a focus on designing inhibitors, including constrained peptides, foldamers and proteomimetic-derived ligands. In doing so, key challenges and major advances in developing generic approaches for the elaboration of PPI inhibitors are highlighted. The challenges faced in developing such ligands as drug leads--and how criteria applied to these may differ from conventional small-molecule drugs--are summarized.
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              Bioisosterism: A Rational Approach in Drug Design.

              George A. Patani, Edmond LaVoie (1996)
              Article 0 comments Cited 152 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (publisher-id): OBCRAK
                Title: Organic & Biomolecular Chemistry
                Abbreviated Title: Org. Biomol. Chem.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1477-0520
                ISSN (Electronic): 1477-0539
                Publication date Created: 2017
                Publication date (Electronic): 2017
                Volume: 15
                Issue: 2
                Pages: 373-378
                Affiliations
                [1 ]Molecular Design and Synthesis
                [2 ]Department of Chemistry
                [3 ]KU Leuven
                [4 ]B-3001 Leuven
                [5 ]Belgium
                [6 ]Biochemistry
                [7 ]Molecular and Structural Biology
                Article
                DOI: 10.1039/C6OB02358D
                SO-VID: 51a71b24-dd7e-4a4d-b11b-f94a9787ec41
                Copyright © © 2017
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