Maike Lenz1, Jan Meisner2, Leann Quertinmont3, Stefan Lutz3, Johannes Kästner2, Bettina M Nestl1. 1. Institute of Technical Biochemistry, Universitaet Stuttgart, Allmandring 31, 70569, Stuttgart, Germany. 2. Institute for Theoretical Chemistry, Universitaet Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany. 3. Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia, 30322, USA.
Abstract
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.
The rapidly growing area of asymmetric imine reduction by n class="Chemical">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.
Authors: James R Marshall; Peiyuan Yao; Sarah L Montgomery; James D Finnigan; Thomas W Thorpe; Ryan B Palmer; Juan Mangas-Sanchez; Richard A M Duncan; Rachel S Heath; Kirsty M Graham; Darren J Cook; Simon J Charnock; Nicholas J Turner Journal: Nat Chem Date: 2020-12-30 Impact factor: 24.427
Authors: Thomas W Thorpe; James R Marshall; Vanessa Harawa; Rebecca E Ruscoe; Anibal Cuetos; James D Finnigan; Antonio Angelastro; Rachel S Heath; Fabio Parmeggiani; Simon J Charnock; Roger M Howard; Rajesh Kumar; David S B Daniels; Gideon Grogan; Nicholas J Turner Journal: Nature Date: 2022-04-06 Impact factor: 49.962
Authors: Sebastian Roth; Peter Stockinger; Jakob Steff; Simon Steimle; Viktor Sautner; Kai Tittmann; Jürgen Pleiss; Michael Müller Journal: Chembiochem Date: 2020-07-02 Impact factor: 3.164