Single-Biocatalyst Synthesis of Enantiopure d-Arylalanines Exploiting an Engineered d-Amino Acid Dehydrogenase

A practical and efficient biocatalytic synthesis of aromatic d‐amino acids has been developed, based on the reductive amination of the corresponding α‐keto acids via a recombinant whole cell system composed of an engineered dehydrogenase and cofactor recycling apparatus. The reaction was shown to gi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis Vol. 358; no. 20; pp. 3298 - 3306
Main Authors: Parmeggiani, Fabio, Ahmed, Syed T., Thompson, Matthew P., Weise, Nicholas J., Galman, James L., Gahloth, Deepankar, Dunstan, Mark S., Leys, David, Turner, Nicholas J.
Format: Journal Article
Language:English
Published: Blackwell Publishing Ltd 20.10.2016
Subjects:
amino acids
asymmetric synthesis
biocatalysis
Catalysis
Catalysts
Derivatives
enzyme catalysis
Enzymes
oxidoreductases
Recombinant
Recycling
Synthesis
Synthesis (chemistry)
ISSN:1615-4150, 1615-4169
Online Access:Get full text
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Summary:A practical and efficient biocatalytic synthesis of aromatic d‐amino acids has been developed, based on the reductive amination of the corresponding α‐keto acids via a recombinant whole cell system composed of an engineered dehydrogenase and cofactor recycling apparatus. The reaction was shown to give excellent enantioselectivity (≥98%) and good yields at the preparative scale across a broad range of substrates. Additionally, the structure of the variant enzyme was solved to allow rationalisation of the observed reaction rates. The engineered whole cell catalyst was also used to mediate the production of d‐phenylalanine derivatives from racemic mixtures and cheaper l‐amino acids by combining it with an enantiocomplementary deaminase.
Bibliography:Royal Society - No. Wolfson Research Merit Award
istex:595996C86C8EFB221A699983888AE987FF83E925
BBSRC - No. grant ref. BB/M017702/1, "Centre for synthetic biology of fine and speciality chemicals"
ArticleID:ADSC201600682
Glaxo-SmithKline (GSK) - No. Strategic Longer and Larger (sLoLa) grant initiative ref. BB/K00199X/1
Biotechnology and Biological Sciences Research Council (BBSRC)
ark:/67375/WNG-4604X4NT-N
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600682