Efficient Tandem Biocatalytic Process for the Kinetic Resolution of Aromatic β-Amino Acids
✍ Scribed by Bian Wu; Wiktor Szymański; Stefaan de Wildeman; Gerrit J. Poelarends; Ben L. Feringa; Dick B. Janssen
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 230 KB
- Volume
- 352
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Abstract
We describe a simple and efficient enzymatic tandem reaction for the preparation of enantiomerically pure β‐phenylalanine and its analogues from the corresponding racemates. In this process, phenylalanine aminomutase (PAM) catalyzes the stereoselective isomerization of (R)‐β‐phenylalanines to (S)‐α‐phenylalanines, which are in situ transformed to cinnamic acids by phenylalanine ammonia lyase (PAL). Preparative scale conversions are done with a mutated PAM with enhanced catalytic activity.
📜 SIMILAR VOLUMES
Chemoenzymatic dynamic kinetic resolution of b-hydroxy nitriles 1 has been carried out using Candida antarctica lipase B and a ruthenium catalyst. The use of a hydrogen source to depress ketone formation in the dynamic kinetic resolution yields the corresponding acetates 2 in good yield and high ena
Scheme 1. Enantioselective synthesis of b-amino acids and nitriles; for R 2 and R 3 see Table 1.