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Published on: August 1, 2018
Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic
Johannes Wunderlich1, Theresa Roß1, Marius Schröder1
1Fakultät Biologie, Chemie und Geologie, Department of Chemistry, Universität Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany.
Abstract:
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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