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Discovery of florylpicoxamid, a mimic of a macrocyclic natural product.

Abstract
Natural products have routinely been used both as sources of and inspiration for new crop protection active ingredients. The natural product UK-2A has potent anti-fungal activity but lacks key attributes for field translation. Post-fermentation conversion of UK-2A to fenpicoxamid resulted in an active ingredient with a new target site of action for cereal and banana pathogens. Here we demonstrate the creation of a synthetic variant of fenpicoxamid via identification of the structural elements of UK-2A that are needed for anti-fungal activity. Florylpicoxamid is a non-macrocyclic active ingredient bearing two fewer stereocenters than fenpicoxamid, controls a broad spectrum of fungal diseases at low use rates and has a concise, scalable route which is aligned with green chemistry principles. The development of florylpicoxamid represents the first example of using a stepwise deconstruction of a macrocyclic natural product to design a fully synthetic crop protection active ingredient.
AuthorsKevin G Meyer, Karla Bravo-Altamirano, Jessica Herrick, Brian A Loy, Chenglin Yao, Ben Nugent, Zachary Buchan, John F Daeuble, Ron Heemstra, David M Jones, Jeremy Wilmot, Yu Lu, Kyle DeKorver, Johnathan DeLorbe, Jared Rigoli
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 50 Pg. 116455 (11 15 2021) ISSN: 1464-3391 [Electronic] England
PMID34757295 (Publication Type: Journal Article)
CopyrightCopyright © 2021 Elsevier Ltd. All rights reserved.
Chemical References
  • Antifungal Agents
  • Biological Products
  • Macrocyclic Compounds
  • Pyridines
  • florylpicoxamid
Topics
  • Antifungal Agents (chemical synthesis, chemistry, pharmacology)
  • Ascomycota (drug effects)
  • Biological Products (chemical synthesis, chemistry, pharmacology)
  • Dose-Response Relationship, Drug
  • Drug Discovery
  • Macrocyclic Compounds (chemical synthesis, chemistry, pharmacology)
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyridines (chemical synthesis, chemistry, pharmacology)
  • Structure-Activity Relationship

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