Synthesis of All Stereoisomers of RK460 and Evaluation of Their Activity and Selectivity as Abscisic Acid Receptor Antagonists

Yu Mikame, Kazuko Yoshida, Daisuke Hashizume, Go Hirai, Kazuo Nagasawa, Hiroyuki Osada, Mikiko Sodeoka

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The PYR/PYL/RCAR protein families have recently emerged as receptors of the phytohormone abscisic acid (ABA, 1), which regulates plant responses to environmental stress. These families have multiple members with different physiological actions, and so selective agonists or antagonists are needed both as tools to elucidate functional differences and as lead compounds for agrochemicals. We previously identified RK460 (rac-3 a) as a PYR1-selective antagonist, and showed that it possesses five stereocenters on a 6,5-cis-bicyclo skeleton. Here, we synthesized all the stereoisomers of RK460 and evaluated their activity towards a panel of receptors. Relative stereochemistry as well as absolute stereochemistry was important for selective action.

Original languageEnglish
Pages (from-to)3496-3500
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number14
DOIs
Publication statusPublished - Mar 7 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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