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

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 synthe...

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Bibliographic Details
Published in:Catalysis letters 2018-12, Vol.148 (12), p.3678-3684
Main Authors: Han, Sang-Woo, Shin, Jong-Shik
Format: Article
Language:English
Subjects:
Alanine
Aliphatic compounds
Amino acids
Cascade chemical reactions
Catalysis
Chemistry
Chemistry and Materials Science
Dehydrogenases
Enantiomers
Industrial Chemistry/Chemical Engineering
Nicotinamide adenine dinucleotide
Organometallic Chemistry
Physical Chemistry
Regeneration
Synthesis
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Summary: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% ee D , 52% isolation yield). Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-018-2565-3