Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.
Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.
Bioorg Chem. 2020 Jan;94:103377. doi: 10.1016/j.bioorg.2019.103377. Epub 2019 Oct 21.
Enzyme catalytic promiscuity is the ability of a single enzyme active site to catalyze several chemical transformations, among them those which are different from natural. We have attempted to use this feature of enzymes in the nucleophilic addition of nitromethane to aldimines (the aza-Henry reaction) whose chemically catalyzed version leads to synthetically useful β-nitroamines. We succeded in obtaining for the first time the desired products in the yields up to 81%. The most efficient proved lipase TL (from Pseudomonas stutzeri) and oxynitrilase from Arabidopsis thaliana. However, all the reactions investigated were non-stereoselective.
酶的催化混杂性是指单个酶活性位点能够催化多种化学转化，其中包括那些与天然过程不同的转化。我们试图利用酶的这一特性，在亚胺的亲核加成反应（氮杂 Henry 反应）中加入硝基甲烷，该反应的化学催化版本可以得到具有合成用途的β-硝基胺。我们首次成功地获得了高达 81%收率的所需产物。最有效的酶是来自假单胞菌（Pseudomonas stutzeri）的脂肪酶 TL 和来自拟南芥（Arabidopsis thaliana）的羟腈酶。然而，所有研究的反应都是非对映选择性的。
