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Biocatalytic Cascade for Synthesis of Sitagliptin Intermediate Employing Coupled Transaminase
Taresh P. Khobragade,Pagar Amol D.,GIRI PRITAM DEVIDAS,SARAKSHARADCHANGDEO,전현우,주상우,고영환,박부수,윤형돈 한국생물공학회 2023 Biotechnology and Bioprocess Engineering Vol.28 No.2
Transaminases (TAs) are employed in synthesizing various enantiopure β‐amino acids, key precursors for various pharmaceuticals. Sitagliptin, an oral hyperglycemic drug, is a well-known example. Herein, we developed the coupled enzyme cascade to synthesize the sitagliptin intermediate by fusing two different TAs to regenerate the amino donor. In a cascade system, ethyl 3-oxo-4-(2,4,5- trifluorophenyl) butanoate (1) was converted by esterase from Pseudomonas stutzeri (EstPS) to respective β-keto acid (2) which was subsequently converted by first TA to sitagliptin intermediate (3) using (S)-α-MBA as an amino donor and the acetophenone formed in the reaction was recycled by the second TA to (S)-α-MBA. A single wholecell system was established by the co-expression of esterase and TA fusion protein. The whole-cell biotransformation reaction was performed with varying substrate concentrations from 50-200 mM. The excellent conversion of the product was achieved, ranging from 62-to 100% at the expense of only 25 mM (S)-α-MBA. Notably, our designed system with fusion protein can produce ~5-fold higher product at the expense of 0.5 equivalent (S)-α-MBA. Finally, a preparative scale reaction was performed with 98% conversion.
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