One-Pot Preparation of d-Amino Acids Through Biocatalytic Deracemization Using Alanine Dehydrogenase and ω-Transaminase

Sang Woo Han, Jong Shik Shin

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

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). Graphical Abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)3678-3684
Number of pages7
JournalCatalysis Letters
Volume148
Issue number12
DOIs
Publication statusPublished - 2018 Dec 1

Bibliographical note

Funding Information:
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.

Publisher Copyright:
© 2018, Springer Science+Business Media, LLC, part of Springer Nature.

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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