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Biocatalytic synthesis of chiral N-functionalized amino acids

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Hyslop_2018_ACIE_Biocatalyticsynthesis_AAM.pdf (1.074Mb)
Date
21/09/2018
Author
Hyslop, Julia
Lovelock, Sarah L
Sutton, Peter
Brown, Kristin K
Watson, Allan J. B.
Roiban, Gheorghe-Doru
Keywords
N-methyl amino acid deyhydrogenases
Ketimine reductases
α-keto amino acids
Biocatalysis
Reductive amination
QD Chemistry
NDAS
SDG 9 - Industry, Innovation, and Infrastructure
Metadata
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Abstract
N-functionalized amino acids are important building blocks for the preparation of diverse bioactive molecules including peptides. The development of sustainable manufacturing routes to chiral N-alkylated amino acids remains a significant challenge in the pharmaceutical and fine chemical industries. Herein we report the discovery of a structurally diverse panel of biocatalysts which catalyze the asymmetric synthesis of N-alkyl amino acids via the reductive coupling of ketones and amines. Reactions have been performed on a gram scale to yield optically pure N-alkyl functionalized products in high yields.
Citation
Hyslop , J , Lovelock , S L , Sutton , P , Brown , K K , Watson , A J B & Roiban , G-D 2018 , ' Biocatalytic synthesis of chiral N-functionalized amino acids ' , Angewandte Chemie International Edition , vol. Early View . https://doi.org/10.1002/anie.201806893
Publication
Angewandte Chemie International Edition
Status
Peer reviewed
DOI
https://doi.org/10.1002/anie.201806893
ISSN
1433-7851
Type
Journal article
Rights
Copyright © 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/anie.201806893
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/18531

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