A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize concession steps, the tactical combination of C-H borylation and a Sigman-Heck transform enabled the convergent, stereocontrolled synthesis of the teleocidins.
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Application of a Cell-Free Synthetic Biology Platform for the Reconstitution of Teleocidin B and UK-2A Precursor Biosynthetic Pathways.
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Crop Health R&D, Corteva Agriscience, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
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School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW, Australia; The Australian Research Council Centre of Excellence in Synthetic Biology, Macquarie Park, NSW, Australia.
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J Nat Prod
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Department of System Chemotherapy and Molecular Sciences, Division of Medicinal Frontier Sciences, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
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Biochem Biophys Res Commun
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Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-Ku, Kyoto, 606-8502, Japan. Electronic address:
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View Article and Find Full Text PDFFunctions, Structures, and Engineering of the Teleocidin Biosynthetic Enzymes.
Chem Pharm Bull (Tokyo)
March 2023
Graduate School of Pharmaceutical Sciences, The University of Tokyo.
Teleocidins are natural products belonging to the indole alkaloid family and show potent protein kinase C activation activity. The structural feature of teleocidins is an indole-fused nine-membered lactam ring structure. Due to their unique structures and strong biological activities, many total synthesis and biosynthetic studies of teleocidins have been performed.
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