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无氰化合成腈的方法:基于水相中肟脱水的生物催化概念。

Synthetic Processes toward Nitriles without the Use of Cyanide: A Biocatalytic Concept Based on Dehydration of Aldoximes in Water.

机构信息

Chair of Industrial Organic Chemistry and Biotechnology, Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615, Bielefeld, Germany.

Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan.

出版信息

Chemistry. 2021 Mar 22;27(17):5313-5321. doi: 10.1002/chem.202001647. Epub 2021 Jan 22.

DOI:10.1002/chem.202001647
PMID:33112445
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8049032/
Abstract

While belonging to the most fundamental functional groups, nitriles represent a class of compound that still raises challenges in terms of an efficient, cost-effective, general and, at the same time, sustainable way for their synthesis. Complementing existing chemical routes, recently a cyanide-free enzymatic process technology based on the use of an aldoxime dehydratase (Oxd) as a biocatalyst component has been developed and successfully applied for the synthesis of a range of nitrile products. In these biotransformations, the Oxd enzymes catalyze the dehydration of aldoximes as readily available substrates to the nitrile products. Herein, these developments with such enzymes are summarized, with a strong focus on synthetic applications. It is demonstrated that this biocatalytic technology has the potential to "cross the bridge" between the production of fine chemicals and pharmaceuticals, on one hand, and bulk and commodity chemicals, on the other.

摘要

尽管腈属于最基本的官能团,但它们仍然是一类在合成方面具有高效、经济、通用且可持续性等方面挑战的化合物。除了现有的化学合成方法,最近开发了一种基于使用醛肟脱水酶 (Oxd) 作为生物催化剂组分的无氰酶法工艺技术,并成功应用于一系列腈产品的合成。在这些生物转化中,Oxd 酶可催化醛肟作为易得的底物脱水转化为腈产物。本文总结了这些酶的应用进展,重点介绍了其在合成方面的应用。结果表明,这种生物催化技术有可能在精细化学品和药物的生产与大宗和商品化学品的生产之间架起“桥梁”。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dbc/8049032/73fd1097ae25/CHEM-27-5313-g005.jpg
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J Org Chem. 2019 Apr 19;84(8):4867-4872. doi: 10.1021/acs.joc.9b00184. Epub 2019 Apr 8.
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