Krongyut Chisanu, Wiriya Nittaya, Saiyasombat Worakrit, Chansaenpak Kantapat, Sripattanakul Sineenat, Kamkaew Anyanee, Lai Rung-Yi
School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima, 30000, Thailand.
Institute of Nutrition, Mahidol University, Phutthamonthon, Nakhon Pathom, 73170, Thailand.
Chembiochem. 2025 Jan 14;26(2):e202400697. doi: 10.1002/cbic.202400697. Epub 2024 Nov 18.
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 HO 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.
4-羟基异苯并二氢吡喃-1-酮属于次生代谢物3,4-二氢异香豆素类。它们具有广泛的生物活性。这些化合物可通过使用高价碘物种或N-溴代琥珀酰亚胺进行卤环化反应，然后水解来合成。然而，这些反应需要特定条件且会产生有毒副产物。在本研究中，不等弯孢菌钒氯过氧化物酶（CiVCPO）通过在柠檬酸盐缓冲液（pH 5）中加入KBr和HO，催化具有不同供电子基团（1 a - 1 e）的2-乙烯基苯甲酸的化学酶促环化反应，以良好的产率生成4-羟基异苯并二氢吡喃-1-酮（3 a - 3 e）。反应混合物含有30%的二甲基亚砜，以提高底物溶解度且不损失酶活性。该条件比化学方法更环保。因此，它为合成4-羟基异苯并二氢吡喃-1-酮提供了一种替代方法。
