Lenz Maike, Meisner Jan, Quertinmont Leann, Lutz Stefan, Kästner Johannes, Nestl Bettina M
Institute of Technical Biochemistry, Universitaet Stuttgart, Allmandring 31, 70569, Stuttgart, Germany.
Institute for Theoretical Chemistry, Universitaet Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany.
Chembiochem. 2017 Feb 1;18(3):253-256. doi: 10.1002/cbic.201600647. Epub 2016 Dec 30.
The rapidly growing area of asymmetric imine reduction by imine reductases (IREDs) has provided alternative routes to chiral amines. Here we report the expansion of the reaction scope of IREDs by showing the stereoselective reduction of 2,2,2-trifluoroacetophenone. Assisted by an in silico analysis of energy barriers, we evaluated asymmetric hydrogenations of carbonyls and imines while considering the influence of substrate reactivity on the chemoselectivity of this novel class of reductases. We report the asymmetric reduction of C=N as well as C=O bonds catalysed by members of the IRED enzyme family.
亚胺还原酶（IREDs）催化的不对称亚胺还原这一快速发展的领域为手性胺提供了替代合成路线。在此，我们报道了通过展示2,2,2-三氟苯乙酮的立体选择性还原，扩大了IREDs的反应范围。借助对能垒的计算机模拟分析，我们评估了羰基和亚胺的不对称氢化反应，同时考虑了底物反应性对这类新型还原酶化学选择性的影响。我们报道了IRED酶家族成员催化的C=N以及C=O键的不对称还原反应。
