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One‐pot Synthesis of 4‐Aminocyclohexanol Isomers by Combining a Keto Reductase and an Amine Transaminase
- Abstract The efficient multifunctionalization by one‐pot or cascade catalytic systems has developed as an important research field, but is often challenging due to incompatibilities or cross‐reactivities of the catalysts leading to side product formation. Herein we report the stereoselective preparation of cis‐ and trans‐4‐aminocyclohexanol from the potentially bio‐based precursor 1,4‐cyclohexanedione. We identified regio‐ and stereoselective enzymes catalyzing reduction and transamination of the diketone, which can be performed in a one‐pot sequential or cascade mode. For this, we identified regioselective keto reductases for the selective mono reduction of the diketone to give 4‐hydroxycyclohexanone. The system is modular and by choosing stereocomplementary amine transaminases, both cis‐ and trans‐4‐aminocyclohexanol were synthesized with good to excellent diastereomeric ratios. Furthermore, we identified an amine transaminase that produces cis‐1,4‐cyclohexanediamine with diastereomeric ratios >98 : 2. These examples highlight that the high selectivity of enzymes enable short and stereoselective cascade multifunctionalizations to generate high‐value building blocks from renewable starting materials. Introduction
Author: | Olha Sviatenko, Nicolás Ríos‐Lombardía, Francisco Morís, Javier González‐Sabín, Kollipara Venkata Manideep, Simon Merdivan, Sebastian Günther, Philipp Süss, Matthias Höhne |
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URN: | urn:nbn:de:gbv:9-opus-39767 |
DOI: | https://doi.org/10.1002/cctc.201900733 |
Parent Title (English): | ChemCatChem |
Publisher: | Wiley |
Place of publication: | Hoboken, New Jersey |
Document Type: | Article |
Language: | English |
Date of first Publication: | 2019/12/02 |
Release Date: | 2020/10/18 |
Tag: | amine transaminase; amino alcohols; asymmetric catalysis; enzyme catalysis; ketoreductase |
GND Keyword: | - |
Volume: | 11 |
Issue: | 23 |
First Page: | 5794 |
Last Page: | 5799 |
Faculties: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie |
Licence (German): | Creative Commons - Namensnennung |