Chemoenzymatic Cyclization by Vanadium Chloroperoxidase for Synthesis of 4-Hydroxyisochroman-1-Ones.

Autor: Krongyut C; School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand., Wiriya N; School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand., Saiyasombat W; School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand.; Institute of Nutrition, Mahidol University, Phutthamonthon, Nakhon Pathom, 73170, Thailand., Chansaenpak K; National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani, 12120, Thailand., Sripattanakul S; School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand., Kamkaew A; School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand., Lai RY; School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand.; Center for Biomolecular Structure, Function and Application, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand.
Jazyk: angličtina
Zdroj: Chembiochem : a European journal of chemical biology [Chembiochem] 2024 Nov 03, pp. e202400697. Date of Electronic Publication: 2024 Nov 03.
DOI: 10.1002/cbic.202400697
Abstrakt: 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 H 2 O 2 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.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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