Selective Enzymatic C-H-Oxyfunctionalization for the Efficient Synthesis of Grevillic Acid

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-28 DOI:10.1002/adsc.202401421

Clemens Cziegler, Benjamin Baumert, Christoffel P. S. Badenhorst, Karsten Siems, Uwe Bornscheuer

引用次数: 0

Abstract

In this study, a selective C-H oxyfunctionalization using an unspecific peroxygenase (UPO) enabled an efficient biosynthetic route for the synthesis of grevillic acid (GA), a natural antioxidant. The route commenced with the release of o-coumaric acid (oCA) from trans-2-coumaric acid glucoside (trans-CAG) using commercially available ꞵ-glucosidase from almonds. In addition, a cis-to-trans photoisomerization of cis-CAG was implemented to increase the synthetic access of oCA. The key step, the para-hydroxylation relative to the existing hydroxyl group of oCA, was accomplished by an UPO with full conversion and 93% isolated yield. Despite its name, the UPO turned out to exhibit excellent regioselectivity in this C-H functionalization, requiring only H2O2 as a cosubstrate.

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选择性酶催化c - h -氧官能化高效合成甘草酸

在这项研究中，利用非特异性过加氧酶（UPO）选择性的C-H氧化功能化为天然抗氧化剂格雷维酸（GA）的合成提供了有效的生物合成途径。该路线开始于从反式-2-香豆酸葡萄糖苷（反式cag）中释放o-香豆酸（oCA），使用市售的ꞵ-杏仁葡萄糖苷酶。此外，还对顺式cag进行顺式-反式光异构化，以增加oCA的合成途径。关键步骤是相对于oCA现有羟基的对羟基化，通过UPO完成，转化率为100%，分离收率为93%。尽管它的名字，UPO被证明在这种C-H功能化中表现出优异的区域选择性，只需要H2O2作为共底物。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.