Carter Eve M, Subrizi Fabiana, Ward John M, Sheppard Tom D, Hailes Helen C
Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ UK.
Department of Biochemical Engineering University College London Gower Street, Bernard Katz Building London WC1E 6BT UK.
ChemCatChem. 2021 Nov 8;13(21):4520-4523. doi: 10.1002/cctc.202101008. Epub 2021 Sep 17.
Transaminase enzymes (TAms) have been widely used for the amination of aldehydes and ketones, often resulting in optically pure products. In this work, transaminases were directly reacted with hydrazones in a novel approach to form amine products. Several substrates were investigated, including those with furan and phenyl moieties. It was determined that the amine yields increased when an additional electrophile was added to the reaction mixture, suggesting that they can sequester the hydrazine released in the reaction. Pyridoxal 5'-phosphate (PLP), a cofactor for transaminases, and polyethylene glycol (PEG)-aldehydes were both found to increase the yield of amine formed. Notably, the amination of ()-(-)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP) hydrazones gave promising results as a method to form chiral β-substituted amines in good yield.
转氨酶（TAms）已被广泛用于醛和酮的胺化反应，常常生成光学纯的产物。在这项工作中，转氨酶以一种新颖的方法与腙直接反应以形成胺产物。研究了几种底物，包括带有呋喃和苯基部分的底物。结果确定，当向反应混合物中添加额外的亲电试剂时，胺产率会提高，这表明它们可以螯合反应中释放的肼。转氨酶的辅因子磷酸吡哆醛（PLP）和聚乙二醇（PEG）-醛均被发现可提高形成的胺的产率。值得注意的是，（）-（-）-1-氨基-2-（甲氧基甲基）吡咯烷（SAMP）腙的胺化反应作为一种以良好产率形成手性β-取代胺的方法给出了有前景的结果。
