Abstract
d-Amino acids are pharmaceutically important building blocks, leading to a great deal of research efforts to develop cost-effective synthetic methods. Preparation of d-amino acids by deracemization has been conceptually attractive owing to facile synthesis of racemic amino acids by Strecker synthesis. Here, we demonstrated biocatalytic deracemization of aliphatic amino acids into d-enantiomers by running cascade reactions; (1) stereoinversion of l-amino acid to a d-form by amino acid dehydrogenase and ω-transaminase and (2) regeneration of NAD+ by NADH oxidase. Under the cascade reaction conditions containing 100 mM isopropylamine and 1 mM NAD+, complete deracemization of 100 mM dl-alanine was achieved after 24 h with 95% reaction yield of d-alanine (> 99% eeD, 52% isolation yield).
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Acknowledgements
This work was funded by the National Research Foundation of Korea under the Basic Science Research Program (2016R1A2B400840). We thank Mrs Sae-Rom Park for technical assistance in the cloning of NOX.
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Han, SW., Shin, JS. One-Pot Preparation of d-Amino Acids Through Biocatalytic Deracemization Using Alanine Dehydrogenase and ω-Transaminase. Catal Lett 148, 3678–3684 (2018). https://doi.org/10.1007/s10562-018-2565-3
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DOI: https://doi.org/10.1007/s10562-018-2565-3