蒙氏假单胞菌ZMU-T06氧化脱氢芳构化合成2-取代喹啉类化合物

Pseudomonas monteilii ZMU-T06 produces 2-substituted quinolines by oxidative dehydroaromatization

摘要:

2-取代喹啉是合成天然产物和药物的重要组成部分。与经典方法相比，2-取代-1,2,3,4-四氢喹啉的脱氢芳构化由于其高原子经济性和可持续性，近年来已成为获得2-取代喹啉的一种有效而直接的方法。然而，现有的化学方法需要使用过渡金属催化剂且反应条件苛刻，相比之下生物催化具有高效、高选择性以及反应条件温和等优点，已经成为有机合成领域的重要方法。本研究通过生物酶挖掘获得一株产单胺氧化酶的蒙氏假单胞菌(Pseudomonas monteilii) ZMU-T06，能够催化2-取代-1,2,3,4-四氢喹啉类化合物脱氢芳构化合成2-取代喹啉类化合物(8个底物，产率为45.7%–48.4%)，并推测了其可能的催化机理，为绿色合成2-取代喹啉类化合物提供新的方法。

Abstract:

2-substituted quinolines are the building blocks for the synthesis of natural products and pharmaceuticals. In comparison with classical methods, dehydroaromatization of 2-substituted-1,2,3,4-tetrahydroquinolines has emerged in recent years as an efficient and straightforward method to synthesize quinolines due to its high atom economy and sustainability. However, existing chemical methods need transition metal catalysts and harsh reaction conditions. Biocatalysis with high efficiency, high selectivity, and mild reaction conditions has become an important method of organic synthesis. We mined a strain Pseudomonas monteilii ZMU-T06 capable of producing monoamine oxidase for the dehydroaromatization of 2-substituted-1,2,3,4-tetrahydroquinolines to synthesize 2-substituted quinolines (8 substrates, yields of 45.7%–48.4%) and then hypothesized the catalytic mechanism, providing a new method for green synthesis of 2-substituted quinolines.