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Asymmetric Reduction of Cyclic Imines by Imine Reductase Enzymes in Non-Conventional Solvents.
- Source :
-
ChemSusChem [ChemSusChem] 2024 Feb 08; Vol. 17 (3), pp. e202301243. Date of Electronic Publication: 2023 Nov 15. - Publication Year :
- 2024
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Abstract
- The first enantioselective reduction of 2-substituted cyclic imines to the corresponding amines (pyrrolidines, piperidines, and azepines) by imine reductases (IREDs) in non-conventional solvents is reported. The best results were obtained in a glycerol/phosphate buffer 1 : 1 mixture, in which heterocyclic amines were produced with full conversions (>99 %), moderate to good yields (22-84 %) and excellent S-enantioselectivities (up to >99 % ee). Remarkably, the process can be performed at a 100 mM substrate loading, which, for the model compound, means a concentration of 14.5 g L <superscript>-1</superscript> . A fed-batch protocol was also developed for a convenient scale-up transformation, and one millimole of substrate 1 a was readily converted into 120 mg of enantiopure amine (S)-2 a with a remarkable 80 % overall yield. This aspect strongly contributes to making the process potentially attractive for large-scale applications in terms of economic and environmental sustainability for a good number of substrates used to produce enantiopure cyclic amines of high pharmaceutical interest.<br /> (© 2023 The Authors. ChemSusChem published by Wiley-VCH GmbH.)
- Subjects :
- Solvents
Stereoisomerism
Amines chemistry
Oxidoreductases
Imines chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1864-564X
- Volume :
- 17
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- ChemSusChem
- Publication Type :
- Academic Journal
- Accession number :
- 37751248
- Full Text :
- https://doi.org/10.1002/cssc.202301243