Asymmetric synthesis of aromatic β-amino acids using ω-transaminase: Optimizing the lipase concentration to obtain thermodynamically unstable β-keto acids.
Synthesized aromatic β-amino acids have recently attracted considerable attention for their application as precursors in many pharmacologically relevant compounds. Previous studies on asymmetric synthesis of aromatic β-amino acids using ω-transaminases could not be done efficiently due to the instability of β-keto acids. In this study, a strategy to circumvent the instability problem of β-keto acids was utilized to generate β-amino acids efficiently via asymmetric synthesis. In this work, thermodynamically stable β-ketoesters were initially converted to β-keto acids using lipase, and the β-keto acids were subsequently aminated using ω-transaminase. By optimizing the lipase concentration, we successfully overcame the instability problem of β-keto acids and enhanced the production of β-amino acids. This strategy can be used as a general approach to efficiently generate β-amino acids from β-ketoesters.
School of Biotechnology, Yeungnam University, Gyeongsan, Gyeongbuk, South Korea.
Sam
S
Mathew
Department of Life Chemistry, Catholic University of Daegu, Daegu, Gyeongbuk, South Korea.
Seong-Su
SS
Jeong
School of Biotechnology, Yeungnam University, Gyeongsan, Gyeongbuk, South Korea.
Taeowan
T
Chung
Department of Life Chemistry, Catholic University of Daegu, Daegu, Gyeongbuk, South Korea. leeshh@cu.ac.kr.
Sang-Hyeup
SH
Lee
Department of Bioscience & Biotechnology, Konkuk University, Seoul, South Korea. hyungdon@konkuk.ac.kr.
Hyungdon
H
Yun
D024322:Amino Acids, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D007651:Keto Acids / Q000737:chemistry*; D008049:Lipase / Q000032:analysis* / Q000378:metabolism; D015394:Molecular Structure; D055550:Protein Stability; D013816:Thermodynamics; D000637:Transaminases / Q000378:metabolism
D024322:Amino Acids, Aromatic; D007651:Keto Acids; D000637:Transaminases; D008049:Lipase
Asymmetric synthesis; Beta amino acids; Biocatalysis; Unnatural amino acid; ω-transaminase