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- Title
Chemoenzymatic Method for Enantioselective Synthesis of (R)‐2‐Phenylglycine and (R)‐2‐Phenylglycine Amide from Benzaldehyde and KCN Using Difference of Enzyme Affinity to the Enantiomers.
- Authors
Kawahara, Nobuhiro; Asano, Yasuhisa
- Abstract
In general, enzymatic and chemoenzymatic methods for asymmetric synthesis of α‐amino acids are performed using highly enantioselective enzymes. The enzymatic reactions using α‐aminonitrile as a starting material have been performed using reaction conditions apart from the chemical Strecker synthesis. We developed a new chemoenzymatic method for the asymmetric synthesis of α‐amino acids from aldehydes and KCN by performing Strecker synthesis and nitrilase reaction in the same reaction mixture. Nitrilase AY487533 that showed rather low enantioselectivity in hydrolysis of 2‐phenylglycinonitrile (2PGN) to 2‐phenylglycine (2PG) was utilized in the hydrolysis of aminonitrile formed from benzaldehyde and KCN via 2PGN by Strecker synthesis, preferentially synthesizing (R)‐2PG with more than 95 % yield and enantiomeric excess (ee). The method was also utilized for the synthesis of (R)‐2‐phenylglycine amide ((R)‐2PGNH2) from benzaldehyde and KCN by the chemoenzymatic reaction in the presence of a mutated nitrilase AY487533W186A, which catalyzes the conversion of 2PGN to 2PGNH2. Taking fewer steps: A new chemoenzymatic method for the asymmetric synthesis of α‐amino acids from aldehydes and KCN by performing Strecker synthesis and nitrilase reaction in the same reaction mixture is developed. This method can be widely utilized to reduce the number of steps in enantioselective synthesis.
- Subjects
PHENYLGLYCINE; ENANTIOSELECTIVE catalysis; BENZALDEHYDE; ENZYMATIC analysis; NITRILASES; ENANTIOMERS; AMINO acids; CHEMICAL affinity
- Publication
ChemCatChem, 2018, Vol 10, Issue 21, p5014
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.201801254