Scalable total synthesis and comprehensive structure–activity relationship studies of the phytotoxin coronatine
Date
16/03/2018Metadata
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Abstract
Natural phytotoxins are valuable starting points for agrochemical design. Acting as a jasmonate agonist, coronatine represents an attractive herbicidal lead with novel mode of action, and has been an important synthetic target for agrochemical development. However, both restricted access to quantities of coronatine and a lack of a suitably scalable and flexible synthetic approach to its constituent natural product components, coronafacic and coronamic acids, has frustrated development of this target. Here, we report gram-scale production of coronafacic acid that allows a comprehensive structure–activity relationship study of this target. Biological assessment of a >120 member library combined with computational studies have revealed the key determinants of potency, rationalising hypotheses held for decades, and allowing future rational design of new herbicidal leads based on this template.
Citation
Littleson , M M , Baker , C M , Dalençon , A J , Frye , E C , Jamieson , C , Kennedy , A R , Ling , K B , McLachlan , M M , Montgomery , M G , Russell , C J & Watson , A J B 2018 , ' Scalable total synthesis and comprehensive structure–activity relationship studies of the phytotoxin coronatine ' , Nature Communications , vol. 9 , 1105 . https://doi.org/10.1038/s41467-018-03443-1
Publication
Nature Communications
Status
Peer reviewed
ISSN
2041-1723Type
Journal article
Rights
Copyright 2018 the Authors. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
Description
The authors thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses, the University of Strathclyde for PhD studentship (M.M.L), and Syngenta for financial and chemical support.Collections
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