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- W4309360646 abstract "(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." @default.
- W4309360646 created "2022-11-26" @default.
- W4309360646 creator A5019384284 @default.
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- W4309360646 date "2022-11-18" @default.
- W4309360646 modified "2023-10-08" @default.
- W4309360646 title "Enantioselective total syntheses of (<i>S</i>)-phosphonothrixin and unexpected cyclic derivative (<i>S</i>)-cyclic phosphonothrixin via enzymatic resolution" @default.
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- W4309360646 doi "https://doi.org/10.1093/bbb/zbac188" @default.
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