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萘的生物催化芳香性破坏环氧化反应和亲核开环反应

Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions.

作者信息

Zhang Wuyuan, Li Huanhuan, Younes Sabry H H, Gómez de Santos Patricia, Tieves Florian, Grogan Gideon, Pabst Martin, Alcalde Miguel, Whitwood Adrian C, Hollmann Frank

机构信息

Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629HZ Delft, The Netherlands.

Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, 32 West 7th Avenue, Tianjin 300308, China.

出版信息

ACS Catal. 2021 Mar 5;11(5):2644-2649. doi: 10.1021/acscatal.0c05588. Epub 2021 Feb 12.

DOI:10.1021/acscatal.0c05588
PMID:33763289
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7976598/
Abstract

Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene synthons. Here, we show that naphthalene epoxides generated by fungal peroxygenases can be subjected to nucleophilic ring opening, yielding non-racemic trans-disubstituted cyclohexadiene derivates, which in turn can be used for further chemical transformations. This approach may represent a promising shortcut for the synthesis of natural products and APIs.

摘要

血红素硫醇盐酶催化的芳香族羟基化反应通过环氧化物中间体进行。这些芳香族环氧化物可能是有机合成中有价值的构建模块，可用于制备一系列手性反式二取代环己二烯合成子。在这里，我们表明，真菌过氧酶生成的萘环氧化物可进行亲核开环反应，生成非外消旋的反式二取代环己二烯衍生物，这些衍生物进而可用于进一步的化学转化。这种方法可能是合成天然产物和活性药物成分的一条有前景的捷径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/35452fde6d91/cs0c05588_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/bb10d44f0bd1/cs0c05588_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/7cfabb86916d/cs0c05588_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/dd78f7a9e88a/cs0c05588_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/de5c69d7ec64/cs0c05588_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/35452fde6d91/cs0c05588_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/bb10d44f0bd1/cs0c05588_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/7cfabb86916d/cs0c05588_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/dd78f7a9e88a/cs0c05588_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/de5c69d7ec64/cs0c05588_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d1/7976598/35452fde6d91/cs0c05588_0005.jpg

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