An efficient and scalable synthesis of a persistent abscisic acid analog (+)-tetralone ABA.
Org Biomol Chem
; 21(14): 3014-3019, 2023 04 05.
Article
em En
| MEDLINE
| ID: mdl-36942670
ABSTRACT
The plant hormone (S)-abscisic acid (ABA) is a signalling molecule found in all plants that triggers plants' responses to environmental stressors such as heat, drought, and salinity. Metabolism-resistant ABA analogs that confer longer lasting effects require multi-step syntheses and high costs that prevent their application in crop protection. To solve this issue, we have developed a two-step, efficient and scalable synthesis of (+)-tetralone ABA from (S)-ABA methyl ester. A challenging three-carbon insertion and a bicyclic ring formation on (S)-ABA methyl ester was achieved through a highly regioselective Knoevenagel condensation, cyclization, and oxidation in one-pot. Further we have studied the biological activity and metabolism of (+)-tetralone ABA in planta and found the analog is hydroxylated similarly to ABA. The biologically active hydroxylated tetralone ABA has greater persistence than 8'-hydroxy ABA as cyclization to the equivalent of phaseic acid is prevented by the aromatic ring. (+)-tetralone ABA complemented the growth retardation of an Arabidopsis ABA-deficient mutant more effectively than (+)-ABA. Taken together, this new synthesis allows the production of the potent ABA agonist efficiently on an industrial scale.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Arabidopsis
/
Proteínas de Arabidopsis
/
Tetralonas
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2023
Tipo de documento:
Article
País de afiliação:
Canadá