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- Title
Biotransformation of β-keto nitriles to chiral ( S)-β-amino acids using nitrilase and ω-transaminase.
- Authors
Mathew, Sam; Nadarajan, Saravanan; Sundaramoorthy, Uthayasuriya; Jeon, Hyunwoo; Chung, Taeowan; Yun, Hyungdon
- 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.
- Subjects
BRADYRHIZOBIUM japonicum; BIOTRANSFORMATION (Metabolism); AMINO acids; CHIRALITY; NITRILASES; AMINOTRANSFERASES
- Publication
Biotechnology Letters, 2017, Vol 39, Issue 4, p535
- ISSN
0141-5492
- Publication type
Article
- DOI
10.1007/s10529-016-2271-4