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Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies

  • Johannes Wunderlich
    Johannes Wunderlich
    Fakultät Biologie, Chemie und Geologie, Department of Chemistry, Universität Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany
  • Theresa Roß
    Theresa Roß
    Fakultät Biologie, Chemie und Geologie, Department of Chemistry, Universität Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany
    More by Theresa Roß
  • Marius Schröder
    Marius Schröder
    Fakultät Biologie, Chemie und Geologie, Department of Chemistry, Universität Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany
  • , and 
  • Frank Hahn*
    Frank Hahn
    Fakultät Biologie, Chemie und Geologie, Department of Chemistry, Universität Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany
    *Email: [email protected]
    More by Frank Hahn
Cite this: Org. Lett. 2020, 22, 13, 4955–4959
Publication Date (Web):June 17, 2020
https://doi.org/10.1021/acs.orglett.0c01348
Copyright © 2020 American Chemical Society

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    Abstract

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    Studies on the biosynthetic processing of polyene thioester intermediates are complicated by limited access to appropriate substrate surrogates. We present a step-economic synthetic access to biomimetic β-ketopolyene thioesters that is based on an Ir-catalyzed reductive Horner–Wadsworth–Emmons olefination. New β-ketotriene and pentaenethioates of pantetheine and N-acetylcysteamine were exemplarily synthesized via short and concise routes. The usefulness of these compounds was demonstrated in an in vitro assay with the ketoreductase domain MycKRB from mycolactone biosynthesis.

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    Cited By

    This article is cited by 7 publications.

    1. Marius Schröder, Theresa Roß, Franziska Hemmerling, Frank Hahn. Studying a Bottleneck of Multimodular Polyketide Synthase Processing: the Polyketide Structure-Dependent Performance of Ketoreductase Domains. ACS Chemical Biology 2022, 17 (5) , 1030-1037. https://doi.org/10.1021/acschembio.2c00047
    2. Sebastian Derra, Julian Hoffmann, Frank Hahn. Synthesis of Biomimetic Thioesters for Studies of Ketoreductase Domains from the Biosynthesis of Cytotoxic Polyketides. Synlett 2023, 25 https://doi.org/10.1055/a-2216-4521
    3. Sebastian Derra, Luca Schlotte, Frank Hahn. Suzuki–Miyaura Reaction in the Presence of N-Acetylcysteamine Thioesters Enables Rapid Synthesis of Biomimetic Polyketide Thioester Surrogates for Biosynthetic Studies. Chemistry 2023, 5 (2) , 1407-1418. https://doi.org/10.3390/chemistry5020096
    4. Aleksander Canko, Georgia D. Athanassopoulou, Vassilis Psycharis, Catherine P. Raptopoulou, Julie M. Herniman, Vasileios Mouchtouris, Angeliki Sofia Foscolos, Elias A. Couladouros, Veroniki P. Vidali. First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B. Organic & Biomolecular Chemistry 2023, 21 (18) , 3761-3765. https://doi.org/10.1039/D3OB00476G
    5. Zhiyong Yin, Daniel Bär, Bertolt Gust, Jeroen S. Dickschat. The substrate scope of dehydratases in antibiotic biosynthesis and their application in kinetic resolutions. Organic & Biomolecular Chemistry 2022, 20 (46) , 9103-9107. https://doi.org/10.1039/D2OB01879A
    6. Lisa Wagner, Theresa Roß, Tim Hollmann, Frank Hahn. Cross-linking of a polyketide synthase domain leads to a recyclable biocatalyst for chiral oxygen heterocycle synthesis. RSC Advances 2021, 11 (33) , 20248-20251. https://doi.org/10.1039/D1RA03692K
    7. Sen Yin, Steffen Friedrich, Vjaceslavs Hrupins, Russell J. Cox. In vitro studies of maleidride-forming enzymes. RSC Advances 2021, 11 (25) , 14922-14931. https://doi.org/10.1039/D1RA02118D

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