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非特异性过氧化物酶催化的制备规模 Achmatowicz 和aza-Achmatowicz 重排反应。

Preparative scale Achmatowicz and aza-Achmatowicz rearrangements catalyzed by unspecific peroxygenase.

机构信息

Department of Chemistry, University of York, York YO10 5DD, UK.

GSK Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK.

出版信息

Org Biomol Chem. 2024 Jul 31;22(30):6149-6155. doi: 10.1039/d4ob00939h.

Abstract

The unspecific peroxygenase (UPO) from (rUPO-PaDa-I-H) is an effective and practical biocatalyst for the oxidative expansion of furfuryl alcohols/amines on a preparative scale, using the Achmatowicz and aza-Achmatowicz reaction. The high activity and stability of the enzyme, which can be produced on a large scale as an air-stable lyophilised powder, renders it a versatile and scalable biocatalyst for the preparation of synthetically valuable 6-hydroxypyranones and dihydropiperidinones. In several cases, the biotransformation out-performed the analogous chemo-catalysed process, and operates under milder and greener reaction conditions.

摘要

(rUPO-PaDa-I-H)中的非特异性过氧化物酶(UPO)是一种有效的、实用的生物催化剂,可用于阿赫马托维奇和氮杂阿赫马托维奇反应,在制备规模上氧化扩展糠醇/胺。该酶具有较高的活性和稳定性,可作为一种空气稳定的冻干粉末大规模生产,使其成为一种多功能、可扩展的生物催化剂,可用于制备具有合成价值的 6-羟基-2-吡喃酮和二氢哌啶酮。在几种情况下,生物转化的效果优于类似的化学催化过程,并且在更温和、更环保的反应条件下进行。

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