Authors
Yifei Hao, Hui Jiang, Na Liu, Xiaoyan Zhang, Yunpeng Bai
Published in
Chembiochem : a European journal of chemical biology. Volume 27. Issue 20. Pages e70575. Oct 28, 2026.
Abstract
Indoxacarb is an oxadiazine insecticide bearing a single stereogenic center, of which only the (S)-enantiomer exhibits insecticidal activity. Therefore, the synthesis of the key intermediate (S)-5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone (2) is crucial for the enantioselective total synthesis of Indoxacarb. In this study, a flavin-containing monooxygenase from Bradyrhizobium sp. 200 (BjFMO) was employed for the asymmetric synthesis of this chiral intermediate, offering a biocatalytic approach as a potential complement to conventional chemical routes. Based on molecular docking and sequence alignment, several amino acid residues located in the FAD and NADPH-binding domains were selected for site-saturation mutagenesis. In combination with rational design, additional positions potentially affecting catalytic activity and stability were subjected to site-directed mutagenesis. Beneficial single mutations were iteratively combined to generate the final variant, BjFMOM9. Under optimal conditions, BjFMOM9 displayed a twofold increase in specific activity compared with the wild type. Its half-life at 40 °C was extended from 1.3 to 3.0 h, and its tolerance toward isopropanol, ethanol, and acetone was markedly enhanced. In a preparative synthesis, BjFMOM9 consistently outperformed the wild type, achieving >80% conversion within 10 h and >90% ee for the (S)-product.
PMID:
42900790
Bibliographic data and abstract were imported from PubMed on 21 Oct 2026.
Read full publication at:
Please sign in
to see all details.
Advertisement
Stats
- Recommendations n/a n/a positive of 0 vote(s)
- Views 9
- Comments 0