Literature DB >> 26667842

InspIRED by Nature: NADPH-Dependent Imine Reductases (IREDs) as Catalysts for the Preparation of Chiral Amines.

Gideon Grogan1, Nicholas J Turner2.   

Abstract

Imine reductases (IREDs) are NADPH-dependent oxidoreductases that catalyse the asymmetric reduction of cyclic prochiral imines to amines, with excellent stereoselectivity. Since their discovery, stereocomplementary IREDs have been applied to the production of both (S) and (R) cyclic secondary amines, and the expansion in gene sequences recently identified has hinted at new substrate ranges that extend into acyclic imines and even suggest the possibility of asymmetric reductive amination from suitable ketone and amine precursors. Structural studies of various IREDs are beginning to reveal the complexities inherent in determining substrate range, stereoselectivity and mechanism in these enzymes, which represent a valuable emerging addition to the toolbox of available biocatalysts for chiral amine production.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  NADPH; amines; biocatalysis; oxidoreductases; stereoselectivity

Year:  2015        PMID: 26667842     DOI: 10.1002/chem.201503954

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  19 in total

Review 1.  The role of biocatalysis in the asymmetric synthesis of alkaloids - an update.

Authors:  Emmanuel Cigan; Bettina Eggbauer; Joerg H Schrittwieser; Wolfgang Kroutil
Journal:  RSC Adv       Date:  2021-08-20       Impact factor: 3.361

Review 2.  Multistep enzyme cascades as a route towards green and sustainable pharmaceutical syntheses.

Authors:  Ana I Benítez-Mateos; David Roura Padrosa; Francesca Paradisi
Journal:  Nat Chem       Date:  2022-05-05       Impact factor: 24.274

3.  Holo Structure and Steady State Kinetics of the Thiazolinyl Imine Reductases for Siderophore Biosynthesis.

Authors:  Kathleen M Meneely; Trey A Ronnebaum; Andrew P Riley; Thomas E Prisinzano; Audrey L Lamb
Journal:  Biochemistry       Date:  2016-09-15       Impact factor: 3.162

Review 4.  Recent advances in imine reductase-catalyzed reactions.

Authors:  Maike Lenz; Niels Borlinghaus; Leonie Weinmann; Bettina M Nestl
Journal:  World J Microbiol Biotechnol       Date:  2017-10-11       Impact factor: 3.312

5.  In vivo plug-and-play: a modular multi-enzyme single-cell catalyst for the asymmetric amination of ketoacids and ketones.

Authors:  Judith E Farnberger; Elisabeth Lorenz; Nina Richter; Volker F Wendisch; Wolfgang Kroutil
Journal:  Microb Cell Fact       Date:  2017-07-28       Impact factor: 5.328

6.  One-step process for production of N-methylated amino acids from sugars and methylamine using recombinant Corynebacterium glutamicum as biocatalyst.

Authors:  Melanie Mindt; Joe Max Risse; Hendrik Gruß; Norbert Sewald; Bernhard J Eikmanns; Volker F Wendisch
Journal:  Sci Rep       Date:  2018-08-27       Impact factor: 4.379

7.  Enantioselective reduction of sulfur-containing cyclic imines through biocatalysis.

Authors:  Nadine Zumbrägel; Christian Merten; Stefan M Huber; Harald Gröger
Journal:  Nat Commun       Date:  2018-05-16       Impact factor: 14.919

8.  Enzymatic and Chemoenzymatic Three-Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines.

Authors:  Vanessa Erdmann; Benjamin R Lichman; Jianxiong Zhao; Robert C Simon; Wolfgang Kroutil; John M Ward; Helen C Hailes; Dörte Rother
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-06       Impact factor: 15.336

9.  A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines.

Authors:  Katherine E Jolley; Michael R Chapman; A John Blacker
Journal:  Beilstein J Org Chem       Date:  2018-08-24       Impact factor: 2.883

Review 10.  NAD(P)H-Dependent Dehydrogenases for the Asymmetric Reductive Amination of Ketones: Structure, Mechanism, Evolution and Application.

Authors:  Mahima Sharma; Juan Mangas-Sanchez; Nicholas J Turner; Gideon Grogan
Journal:  Adv Synth Catal       Date:  2017-05-11       Impact factor: 5.837

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