Chemoenzymatic Cyclization by Vanadium Chloroperoxidase for Synthesis of 4-Hydroxyisochroman-1-Ones
Issued Date
2024-01-01
Resource Type
ISSN
14394227
eISSN
14397633
Scopus ID
2-s2.0-85209815340
Pubmed ID
39489699
Journal Title
ChemBioChem
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SCOPUS
Bibliographic Citation
ChemBioChem (2024)
Suggested Citation
Krongyut C., Wiriya N., Saiyasombat W., Chansaenpak K., Sripattanakul S., Kamkaew A., Lai R.Y. Chemoenzymatic Cyclization by Vanadium Chloroperoxidase for Synthesis of 4-Hydroxyisochroman-1-Ones. ChemBioChem (2024). doi:10.1002/cbic.202400697 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/102197
Title
Chemoenzymatic Cyclization by Vanadium Chloroperoxidase for Synthesis of 4-Hydroxyisochroman-1-Ones
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Abstract
4-Hydroxyisochroman-1-ones belong to the class of the secondary metabolite 3,4-dihydroisocoumarins. They exhibit a wide range of biological activities. These compounds can be synthesized through halocyclization using hypervalent iodine species or N-bromosuccinimide, followed by hydrolysis. Nonetheless, the reactions required specific conditions and generated toxic byproducts. In this study, Curvularia inaequalis vanadium chloroperoxidase (CiVCPO) catalyzed the chemoenzymatic cyclization of 2-vinylbenzoic acids with different electron-donating groups (1 a–1 e) to produce good yields of 4-hydroxyisochroman-1-ones (3 a–3 e) by adding KBr and H2O2 in citrate buffer (pH 5). The reaction mixture contained 30 % DMSO to improve substrate solubility without enzyme activity loss. The condition is more environmentally friendly than chemical methods. Therefore, it offers an alternative approach for synthesizing 4-hydroxyisochroman-1-ones.