title: Biotransformation of β-keto nitriles to chiral (S)-β-amino acids using nitrilase and ω-transaminase.
abstract: OBJECTIVE
  To enzymatically synthesize enantiomerically pure β-amino acids from β-keto nitriles using nitrilase and ω-transaminase.
  
  
  RESULTS
  An enzyme cascade system was designed where in β-keto nitriles are initially hydrolyzed to β-keto acids using nitrilase from Bradyrhizobium japonicum and subsequently β-keto acids were converted to β-amino acids using ω-transaminases. Five different ω-transaminases were tested for this cascade reaction, To enhance the yields of β-amino acids, the concentrations of nitrilase and amino donor were optimized. Using this enzymatic reaction, enantiomerically pure (S)-β-amino acids (ee > 99%) were generated. As nitrilase is the bottleneck in this reaction, molecular docking analysis was carried out to depict the poor affinity of nitrilase towards β-keto acids.
  
  
  CONCLUSIONS
  A novel enzymatic route to generate enantiomerically pure aromatic (S)-β-amino acids from β-keto nitriles is demonstrated for the first time.
authors.affiliation: Department of Biochemistry, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Groningen, The Netherlands.
authors.forename: Sam
authors.initials: S
authors.lastname: Mathew
authors.affiliation: Department of Bioscience and Biotechnology, Konkuk University, Seoul, 05029, Korea.
authors.forename: Saravanan Prabhu
authors.initials: SP
authors.lastname: Nadarajan
authors.affiliation: Department of Bioscience and Biotechnology, Konkuk University, Seoul, 05029, Korea.
authors.forename: Uthayasuriya
authors.initials: U
authors.lastname: Sundaramoorthy
authors.affiliation: Department of Bioscience and Biotechnology, Konkuk University, Seoul, 05029, Korea.
authors.forename: Hyunwoo
authors.initials: H
authors.lastname: Jeon
authors.affiliation: School of Biotechnology, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Korea.
authors.forename: Taeowan
authors.initials: T
authors.lastname: Chung
authors.affiliation: Department of Bioscience and Biotechnology, Konkuk University, Seoul, 05029, Korea. hyungdon@konkuk.ac.kr.
authors.forename: Hyungdon
authors.initials: H
authors.lastname: Yun
mesh_terms: D000596:Amino Acids / Q000378:metabolism*; D000619:Aminohydrolases / Q000378:metabolism*; D001426:Bacterial Proteins / Q000378:metabolism; D001711:Biotransformation; D020369:Bradyrhizobium / Q000201:enzymology; D057075:Enzyme Assays; D004926:Escherichia coli; D006868:Hydrolysis; D062105:Molecular Docking Simulation; D009570:Nitriles / Q000378:metabolism*; D013237:Stereoisomerism; D000637:Transaminases / Q000378:metabolism*
chemical_list: D000596:Amino Acids; D001426:Bacterial Proteins; D009570:Nitriles; D000637:Transaminases; D000619:Aminohydrolases; C021867:nitrilase
keywords: Asymmetric synthesis; Molecular docking; Nitrilase; β-Amino acids; β-Keto acids; β-Keto nitriles; ω-Transaminase