Recent Advances in Imine Reductase-catalyzed Reactions

Overview

Journal World J Microbiol Biotechnol

Publisher Springer

Specialties Biotechnology
Microbiology

Date 2017 Oct 13

PMID 29022156

Citations 18

Authors

Maike Lenz

Niels Borlinghaus

Leonie Weinmann

Bettina M Nestl

Affiliations

Soon will be listed here.

Abstract

Imine reductases are nicotinamide-dependent enzymes that catalyze the asymmetric reduction of various imines to the corresponding amine products. Owing to the increasing roles of chiral amines and heterocyclic compounds as intermediates for pharmaceuticals, the demand for novel selective synthesis strategies is vitally important. Recent studies have demonstrated the discovery and structural characterization of a number of stereoselective imine reductase enzymes. Here, we highlight recent progress in applying imine reductases for the formation of chiral amines and heterocycles. It particularly focuses on the utilization of imine reductases in reductive aminations of aldehydes and ketones with various amine nucleophiles, one of the most powerful reactions in the synthesis of chiral amines. Second, we report on the synthesis of saturated substituted N-heterocycles by combining them with further biocatalysts, such as carboxylic acid reductases, oxidases or transaminases. Finally, we summarize the latest applications of imine reductases in the promiscuous asymmetric hydrogenation of a highly reactive carbonyl compound and the engineering of the cofactor specificity from NADPH to NADH.

Citing Articles

In situ characterization of amine-forming enzymes shows altered oligomeric state.

Caparco A, Bommarius B, Ducrot L, Champion J, Vergne-Vaxelaire C, Bommarius A Protein Sci. 2024; 34(1):e5248.

PMID: 39720905 PMC: 11669115. DOI: 10.1002/pro.5248.

Evolutionary insights into the stereoselectivity of imine reductases based on ancestral sequence reconstruction.

Zhu X, Zheng W, Xia Z, Chen X, Jin T, Ding X Nat Commun. 2024; 15(1):10330.

PMID: 39609402 PMC: 11605051. DOI: 10.1038/s41467-024-54613-3.

ThermoLink: Bridging disulfide bonds and enzyme thermostability through database construction and machine learning prediction.

Xu R, Pan Q, Zhu G, Ye Y, Xin M, Wang Z Protein Sci. 2024; 33(9):e5097.

PMID: 39145402 PMC: 11325166. DOI: 10.1002/pro.5097.

The Discovery of Imine Reductases and their Utilisation for the Synthesis of Tetrahydroisoquinolines.

Cardenas-Fernandez M, Roddan R, Carter E, Hailes H, Ward J ChemCatChem. 2023; 15(3):e202201126.

PMID: 37081856 PMC: 10107726. DOI: 10.1002/cctc.202201126.

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity.

Hecko S, Schiefer A, Badenhorst C, Fink M, Mihovilovic M, Bornscheuer U Chem Rev. 2023; 123(6):2832-2901.

PMID: 36853077 PMC: 10037340. DOI: 10.1021/acs.chemrev.2c00304.

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