Organic Acid to Nitrile: A Chemoenzymatic Three-Step Route,Advanced Synthesis & Catalysis

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Organic Acid to Nitrile: A Chemoenzymatic Three-Step Route
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-30 , DOI: 10.1002/adsc.202201053
Margit Winkler _{1,

2} , Melissa Horvat ₁ , Astrid Schiefer ₃ , Victoria Weilch ₁ , Florian Rudroff ₃ , Miroslav Pátek ₄ , Ludmila Martínková ₄

Affiliation

Various widely applied compounds contain cyano-groups, and this functional group serves as a chemical handle for a whole range of different reactions. We report a cyanide free chemoenzymatic cascade for nitrile synthesis. The reaction pathway starts with a reduction of carboxylic acid to aldehyde by carboxylate reductase enzymes (CARs) applied as living cell biocatalysts. The second – chemical – step includes in situ oxime formation with hydroxylamine. The final direct step from oxime to nitrile is catalyzed by aldoxime dehydratases (Oxds). With compatible combinations of a CAR and an Oxd, applied in one-pot two-step reactions, several aliphatic and aryl-aliphatic target nitriles were obtained in more than 80% conversion. Phenylacetonitrile, for example, was prepared in 78% isolated yield. This chemoenzymatic route does not require cyanide salts, toxic metals, or undesired oxidants in contrast to entirely chemical procedures.

中文翻译：

有机酸制腈：化学酶促三步路线

各种广泛应用的化合物都含有氰基，该官能团可作为各种不同反应的化学手柄。我们报告了用于腈合成的无氰化物化学酶促级联。反应途径始于通过用作活细胞生物催化剂的羧酸还原酶 (CAR) 将羧酸还原为醛。第二个——化学——步骤包括原位与羟胺形成肟。从肟到腈的最后直接步骤是由醛肟脱水酶 (Oxds) 催化的。使用 CAR 和 Oxd 的相容组合，应用于一锅两步反应，以超过 80% 的转化率获得了几种脂肪族和芳基-脂肪族目标腈。例如，苯乙腈的分离产率为 78%。与完全化学过程相比，这种化学酶促途径不需要氰化物盐、有毒金属或不需要的氧化剂。

更新日期：2022-11-30

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