Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization

Löwe J, Ingram AA, Gröger H (2018)
BIOORGANIC & MEDICINAL CHEMISTRY 26(7): 1387-1392.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
In recent years, the reductive amination of ketones in the presence of amine dehydrogenases emerged as an attractive synthetic strategy for the enantioselective preparation of amines starting from ketones, an ammonia source, a reducing reagent and a cofactor, which is recycled in situ by means of a second enzyme. Current challenges in this field consists of providing a broad synthetic platform as well as process development including enzyme immobilization. In this contribution these issues are addressed. Utilizing the amine dehydrogenase EsLeuDH-DM as a mutant of the leucine dehydrogenase from Exigobacterium sibiricum, a range of aryl-substituted ketones were tested as substrates revealing a broad substrate tolerance. Kinetics as well as inhibition effects were also studied and the suitability of this method for synthetic purpose was demonstrated with acetophenone as a model substrate. Even at an elevated substrate concentration of 50 mM, excellent conversion was achieved. In addition, the impact of water-miscible co-solvents was examined, and good activities were found when using DMSO of up to 30% (v/v). Furthermore, a successful immobilization of the EsLeuDH-DM was demonstrated utilizing a hydrophobic support and a support for covalent binding, respectively, as a carrier. (C) 2017 Elsevier Ltd. All rights reserved.
Stichworte
Biocatalysis; Reductive amination; Amine dehydrogenase; Exigobacterium; sibiricum; Immobilization
Erscheinungsjahr
2018
Zeitschriftentitel
BIOORGANIC & MEDICINAL CHEMISTRY
Band
26
Ausgabe
7
Seite(n)
1387-1392
ISSN
0968-0896
eISSN
1464-3391
Page URI
https://pub.uni-bielefeld.de/record/2920277

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Löwe J, Ingram AA, Gröger H. Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization. BIOORGANIC & MEDICINAL CHEMISTRY. 2018;26(7):1387-1392.
Löwe, J., Ingram, A. A., & Gröger, H. (2018). Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization. BIOORGANIC & MEDICINAL CHEMISTRY, 26(7), 1387-1392. doi:10.1016/j.bmc.2017.12.005
Löwe, J., Ingram, A. A., and Gröger, H. (2018). Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization. BIOORGANIC & MEDICINAL CHEMISTRY 26, 1387-1392.
Löwe, J., Ingram, A.A., & Gröger, H., 2018. Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization. BIOORGANIC & MEDICINAL CHEMISTRY, 26(7), p 1387-1392.
J. Löwe, A.A. Ingram, and H. Gröger, “Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization”, BIOORGANIC & MEDICINAL CHEMISTRY, vol. 26, 2018, pp. 1387-1392.
Löwe, J., Ingram, A.A., Gröger, H.: Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization. BIOORGANIC & MEDICINAL CHEMISTRY. 26, 1387-1392 (2018).
Löwe, Jana, Ingram, Aaron A., and Gröger, Harald. “Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization”. BIOORGANIC & MEDICINAL CHEMISTRY 26.7 (2018): 1387-1392.

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