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

Autor: Meyer KG; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA. Electronic address: kevin.meyer@corteva.com., Bravo-Altamirano K; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Herrick J; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Loy BA; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Yao C; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Nugent B; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Buchan Z; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Daeuble JF; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Heemstra R; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Jones DM; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Wilmot J; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Lu Y; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., DeKorver K; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., DeLorbe J; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA., Rigoli J; Corteva Agriscience, 9330 Zionsville Road, Indianapolis, IN 46268, USA.
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2021 Nov 15; Vol. 50, pp. 116455. Date of Electronic Publication: 2021 Oct 23.
DOI: 10.1016/j.bmc.2021.116455
Abstrakt: 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.
(Copyright © 2021 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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