Xiang Haoyue, Ferla Salvatore, Varricchio Carmine, Brancale Andrea, Brown Nicola L, Black Gary W, Turner Nicholas J, Castagnolo Daniele
Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.
Medical School, Faculty of Medicine, Health and Life Science, Swansea University, Swansea SA2 8PP, U.K.
ACS Catal. 2023 Feb 22;13(5):3370-3378. doi: 10.1021/acscatal.2c05902. eCollection 2023 Mar 3.
The oxidative aromatization of aliphatic -heterocycles is a fundamental organic transformation for the preparation of a diverse array of heteroaromatic compounds. Despite many attempts to improve the efficiency and practicality of this transformation, most synthetic methodologies still require toxic and expensive reagents as well as harsh conditions. Herein, we describe two enzymatic strategies for the oxidation of 1,2,3,4-tetrahydroquinolines (THQs) and -cyclopropyl--alkylanilines into quinolines and 2-quinolones, respectively. Whole cells and purified monoamine oxidase (MAO-N) enzymes were used to effectively catalyze the biotransformation of THQs into the corresponding aromatic quinoline derivatives, while -cyclopropyl--alkylanilines were converted into 2-quinolone compounds through a horseradish peroxidase (HRP)-catalyzed annulation/aromatization reaction followed by Fe-mediated oxidation.
脂肪族杂环的氧化芳构化是制备各种杂芳族化合物的一种基本有机转化反应。尽管人们多次尝试提高这种转化反应的效率和实用性，但大多数合成方法仍然需要使用有毒且昂贵的试剂以及苛刻的反应条件。在此，我们描述了两种酶促策略，分别将1,2,3,4-四氢喹啉（THQs）和环丙基烷基苯胺氧化为喹啉和2-喹诺酮。使用全细胞和纯化的单胺氧化酶（MAO-N）有效地催化THQs生物转化为相应的芳香喹啉衍生物，而环丙基烷基苯胺则通过辣根过氧化物酶（HRP）催化的环化/芳构化反应，随后经铁介导的氧化反应转化为2-喹诺酮化合物。
