Journal
CATALYSIS SCIENCE & TECHNOLOGY
Volume 9, Issue 15, Pages 4083-4090Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cy01004a
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Funding
- Spanish Ministry of Economy and Competitiveness (MINECO) [CTQ2016-75752-R]
- MINECO within the FPI program
- EPSRC [EP/S01778X/1] Funding Source: UKRI
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The biocatalytic stereocontrolled synthesis of various acyclic anti- or syn-alpha-alkyl-beta-amino amides through a dynamic kinetic resolution strategy is demonstrated. A series of commercially available and in-house transaminases (TAs) were employed to perform the transamination of a series of chemically synthesized racemic alpha-alkyl-beta-keto amides. Among them, commercial (R)-selective TAs showed the best activities and selectivities, giving access preferentially to the anti-diastereoisomers with low to high diastereomeric ratios (up to 96%) and excellent enantiomeric excess (>99%). The stereoselective biotransamination experiments were successfully demonstrated at a semi-preparative scale (25 mM, 100 mg substrate), leading to the corresponding optically active alpha-alkyl-beta-amino amides in 45-90% isolated yields after a simple liquid-liquid extraction protocol.
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