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

IF 2.6 4区 生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
ChemBioChem Pub Date : 2024-11-03 DOI:10.1002/cbic.202400697
Chisanu Krongyut, Nittaya Wiriya, Worakrit Saiyasombat, Kantapat Chansaenpak, Sineenat Sripattanakul, Anyanee Kamkaew, Rung-Yi Lai
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引用次数: 0

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.

利用氯过氧化钒酶的化学合成环化作用合成 4-羟基异苯并二氢吡喃-1-酮。
4-羟基异苯并吡喃-1-酮属于次级代谢产物 3,4-二氢异香豆素类。它们具有广泛的生物活性。这些化合物可以通过使用高价碘或 N-溴代丁二酰亚胺进行卤代环化,然后进行水解来合成。不过,这些反应需要特定的条件,并会产生有毒的副产品。在本研究中,Curvularia inaequalis 氯过氧化钒酶(CiVCPO)在柠檬酸缓冲液(pH 值为 5)中加入 KBr 和 H2O2,催化了具有不同电子奉献基团的 2-乙烯基苯甲酸(1a-1e)的化学酶环化反应,生成了产率较高的 4-羟基异苯并吡喃-1-酮(3a-3e)。反应混合物中含有 30% 的二甲基亚砜(DMSO),以提高底物的溶解度而不损失酶的活性。这种方法比化学方法更环保。因此,它为合成 4-羟基异苯并吡喃-1-酮提供了一种替代方法。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
ChemBioChem
ChemBioChem 生物-生化与分子生物学
CiteScore
6.10
自引率
3.10%
发文量
407
审稿时长
1 months
期刊介绍: ChemBioChem (Impact Factor 2018: 2.641) publishes important breakthroughs across all areas at the interface of chemistry and biology, including the fields of chemical biology, bioorganic chemistry, bioinorganic chemistry, synthetic biology, biocatalysis, bionanotechnology, and biomaterials. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and supported by the Asian Chemical Editorial Society (ACES).
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