A scalable synthesis of (+)‐coronafacic acid

Kato, Norihiro; Miyagawa, Saki; Nomoto, Haruna; Nakayama, Misuzu; Iwashita, Makoto

doi:10.1002/chir.23172

Cited by 7 publications

(5 citation statements)

References 26 publications

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“…COR is widely used in JA bioscience instead of JA because of the chemical stability of bioactive (7R, 3R)-form, and its most important contribution so far has been the development of the coi1-1 mutant, which incorporates a mutation in gene encoding the COI1 protein (a component of COI1-JAZ coreceptor) and is insensitive to COR [23]. Today, COR is considered as a structural and functional mimic of JA-Ile, and has been accessible in multigram quantities and good optical purity since the landmark work of Watson's and Ueda's groups [24][25][26].…”

Section: The Conventional Chemical Tools For Jasmonate Biosciencementioning

confidence: 99%

Recent Advances in Plant Chemical Biology of Jasmonates

Ueda

Kaji

Kozaki

2020

IJMS

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Lipid-derived plant hormone jasmonates are implicated in plant growth, reproductive performance, senescence, secondary metabolite productions, and defense against both necrotrophic pathogens and feeding insects. A major jasmonate is (+)-7-iso-jasmonoyl-l-isoleucine (JA-Ile), which is perceived by the unique COI1-JAZ coreceptor system. Recent advances in plant chemical biology have greatly informed the bioscience of jasmonate, including the development of chemical tools such as the antagonist COR-MO; the agonist NOPh; and newly developed jasmonates, including JA-Ile-macrolactone and 12-OH-JA-Ile. This review article summarizes the current status of plant chemical biology as it pertains to jasmonates, and offers some perspectives for the future.

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Section: The Conventional Chemical Tools For Jasmonate Biosciencementioning

confidence: 99%

Recent Advances in Plant Chemical Biology of Jasmonates

Ueda

Kaji

Kozaki

2020

IJMS

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“…Enough amount of the stable stereoisomers of 3 was achieved by gram-scale racemic CFA synthesis and subsequent optical resolution, epimerization, and separation of diastereomers (Supplementary Fig. 1a) [27][28][29] . The optical purities of four CFAs (3-3c) were determined by chiral HPLC analyses 30 .…”

Section: Resultsmentioning

confidence: 99%

Subtype-selective agonists of plant hormone co-receptor COI1-JAZs identified from the stereoisomers of coronatine

et al. 2023

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Severe genetic redundancy is particularly clear in gene families encoding plant hormone receptors, each subtype sharing redundant and specific functions. Genetic redundancy of receptor family members represents a major challenge for the functional dissection of each receptor subtype. A paradigmatic example is the perception of the hormone (+)-7-iso-jasmonoyl-L-isoleucine, perceived by several COI1-JAZ complexes; the specific role of each receptor subtype still remains elusive. Subtype-selective agonists of the receptor are valuable tools for analyzing the responses regulated by individual receptor subtypes. We constructed a stereoisomer library consisting of all stereochemical isomers of coronatine (COR), a mimic of the plant hormone (+)-7-iso-jasmonoyl-L-isoleucine, to identify subtype-selective agonists for COI1-JAZ co-receptors in Arabidopsis thaliana and Solanum lycopersicum. An agonist selective for the Arabidopsis COI1-JAZ9 co-receptor efficiently revealed that JAZ9 is not involved in most of the gene downregulation caused by COR, and the degradation of JAZ9-induced defense without inhibiting growth.

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“…All chemical reagents and solvents were obtained from commercial suppliers (Wako Pure Chemical Industries Co. Ltd., Nacalai Tesque Co., Ltd., Watanabe Chemical Industries Co. Ltd., Thermo Fisher Scientific K.K., GE Healthcare) and used without further purification. Coronatine (COR) and (+)- 7 -iso - JA-L-Ile (JA-Ile) were prepared as previously described 1 , 36 , 37 . DNA purification was accomplished using a GENE PERP STAR PI-80X (KURABO, Osaka, Japan).…”

Section: Methodsmentioning

confidence: 99%

Extended JAZ degron sequence for plant hormone binding in jasmonate co-receptor of tomato SlCOI1-SlJAZ

Saito

Hayashi

Nomoto

et al. 2021

Sci Rep

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Abstract(+)-7-iso-Jasmonoyl-l-isoleucine (JA-Ile) is a lipid-derived phytohormone implicated in plant development, reproduction, and defense in response to pathogens and herbivorous insects. All these effects are instigated by the perception of JA-Ile by the COI1-JAZ co-receptor in the plant body, which in Arabidopsis thaliana is profoundly influenced by the short JAZ degron sequence (V/L)P(Q/I)AR(R/K) of the JAZ protein. Here, we report that SlJAZ-SlCOI1, the COI1-JAZ co-receptor found in the tomato plant, relies on the extended JAZ degron sequence (V/L)P(Q/I)AR(R/K)XSLX instead of the canonical JAZ degron. This finding illuminates our understanding of the mechanism of ligand perception by JA-Ile in this plant, and will inform both efforts to improve it by genetic modification of the SlCOI1-SlJAZ co-receptor, and the development of the synthetic agonists/antagonists.

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A scalable synthesis of (+)‐coronafacic acid

Cited by 7 publications

References 26 publications

Recent Advances in Plant Chemical Biology of Jasmonates

Recent Advances in Plant Chemical Biology of Jasmonates

Subtype-selective agonists of plant hormone co-receptor COI1-JAZs identified from the stereoisomers of coronatine

Extended JAZ degron sequence for plant hormone binding in jasmonate co-receptor of tomato SlCOI1-SlJAZ

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