| Autor: |
Koki, Nakamura, Yoshitaka, Matsushima |
| Rok vydání: |
2022 |
| Předmět: |
|
| Zdroj: |
Bioscience, Biotechnology, and Biochemistry. 87:138-147 |
| ISSN: |
1347-6947 |
| Popis: |
(S)-Phosphonothrixin is a phosphonate natural product produced by Saccharothrix sp. ST-888 that exhibits herbicidal activity. The previously reported asymmetric synthesis of (S)-phosphonothrixin is laborious and difficult to reproduce. In this study, we developed a scalable and concise enantioselective total synthesis of (S)-phosphonothrixin via two different synthetic routes by the enzymatic resolution of a known racemic epoxy alcohol. The second-generation synthesis was more efficient in terms of the overall yield (15%) and the number of steps (7) and afforded a unique cyclic phosphonate (phostone) as the product of the C–P bond formation reaction, which was converted to (S)-cyclic phosphonothrixin. Both (S)-phosphonothrixin and (S)-cyclic phosphonothrixin induced chlorosis in the plant Arabidopsis thaliana. However, (S)-cyclic phosphonothrixin exhibited lower activity than (S)-phosphonothrixin owing to its fixed conformation, as evidenced by a structure–activity relationship study. This study paves the way for the elucidation of the detailed mode of action of (S)-phosphonothrixin. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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