Department of Biochemical Sciences "Alessandro Rossi Fanelli", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
Center for Life Nano Science@Sapienza, Istituto Italiano Di Tecnologia, V.le Regina Elena 291, 00161 Rome, Italy.
Biomolecules. 2021 Oct 18;11(10):1540. doi: 10.3390/biom11101540.
Aldehydes are a class of carbonyl compounds widely used as intermediates in the pharmaceutical, cosmetic and food industries. To date, there are few fully enzymatic methods for synthesizing these highly reactive chemicals. In the present work, we explore the biocatalytic potential of an amino oxidase extracted from the etiolated shoots of for the synthesis of value-added aldehydes, starting from the corresponding primary amines. In this frame, we have developed a completely chromatography-free purification protocol based on crossflow ultrafiltration, which makes the production of this enzyme easily scalable. Furthermore, we determined the kinetic parameters of the amine oxidase toward 20 differently substituted aliphatic and aromatic primary amines, and we developed a biocatalytic process for their conversion into the corresponding aldehydes. The reaction occurs in aqueous media at neutral pH in the presence of catalase, which removes the hydrogen peroxide produced during the reaction itself, contributing to the recycling of oxygen. A high conversion (>95%) was achieved within 3 h for all the tested compounds.
醛类是一类广泛用作药物、化妆品和食品工业中间体的羰基化合物。迄今为止,很少有完全酶法合成这些高反应性化学物质的方法。在本工作中,我们探索了从黄化芽中提取的胺氧化酶在合成有价值的醛类方面的生物催化潜力,这些醛类是从相应的伯胺开始合成的。为此,我们开发了一种完全无色谱的纯化方案,基于错流超滤,这使得该酶的生产很容易规模化。此外,我们确定了胺氧化酶对 20 种不同取代的脂肪族和芳香族伯胺的动力学参数,并开发了一种生物催化方法,将它们转化为相应的醛类。该反应在中性 pH 的水相中进行,同时存在过氧化氢酶,它可以去除反应过程中产生的过氧化氢,有助于氧气的循环利用。所有测试的化合物在 3 小时内都实现了>95%的高转化率。