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    Home > Chemicals Industry > Chemical Technology > Scientists use chemical catalytic reductive amination to achieve efficient synthesis of unnatural amino acids

    Scientists use chemical catalytic reductive amination to achieve efficient synthesis of unnatural amino acids

    • Last Update: 2022-05-20
    • Source: Internet
    • Author: User
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    Recently, the team of Yin Qin, associate professor of School of Pharmacy, Shenzhen University of Technology, Chinese Academy of Sciences (tentative name), associate researcher of Institute of Biomedicine and Technology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences, and Zhang Xumu, professor of Southern University of Science and Technology, cooperated on the basis of previous cooperative research (J 2018, 140, 2024.
    ; Angew.
    Chem.
    Int.
    Ed.
    2018, 57, 14193.
    ; Angew.
    Chem.
    Int.
    Ed.
    2020, 59, 5321.
    ; Org.
    Lett.
    2020, 22, 2707.
    ; Org.
    Lett.
    2020, 22, 6479.
    ; Chem.
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    2022, 58, 513.
    ), further explored and realized the direct asymmetric reduction between challenging keto acid derivatives and ammonium salts Amination reaction

    .
    This reaction can provide a chemically catalyzed new route to directly construct optically pure non-natural chiral α-NH
    2 -carboxylic acids, which can be complementary to biocatalysis
    .
    Relevant research results were published in Angew.
    Chem.
    Int.
    Ed

    .

    2

    Chiral unnatural α-amino acids play a very important role in biology, biochemistry, medicine and materials science.
    For example, some d-phenylglycine compounds have been widely used in the production of different types of β-lactam antibiotics

    .
    With the rapid development of peptide drugs, replacing some natural α-amino acids in peptide molecules with non-natural α-amino acids is expected to further enrich the diversity of peptide molecules and obtain peptide drugs with better activity and pharmacokinetic properties

    .
    In addition, chiral unnatural α-amino acids can also be easily converted into some chiral auxiliaries and catalysts, which can be used in asymmetric synthesis

    .
    Therefore, it is of great significance to develop efficient and practical methods to obtain chiral non-natural α-amino acids

    .

    Biocatalysis provides a variety of means for the synthesis of unnatural α-amino acids, usually without the manipulation of protecting groups and under mild conditions
    .
    In contrast, chemical catalysis methods often have certain advantages in substrate universality and reaction scale

    .
    However, most of the reported chemical catalytic synthesis methods of optically pure α-amino acids require pre-preparation of nitrogen-containing substrates with protective groups, resulting in the generation of amino acid derivatives with protective groups on the nitrogen, and additional deprotection operations are required to obtain more Valuable alpha-NH2
    - carboxylic acids
    .
    Based on the previous research results, the researchers explored the reductive amination reaction between a simple and readily available ketoamide and cheap ammonium acetate.
    Under the catalysis of a chiral ruthenium catalyst, optically pure non-natural α-NH with diverse structures can be prepared in one step.
    2 -Carboxylic acid derivatives have very good generality (48 examples), and related research is expected to be applied in the research and development of amino acid drugs
    .

    2 2

    Relevant research work has been funded by the National Natural Science Foundation of China, the Natural Science "Outstanding Youth" Fund of Guangdong Province, and the Start-up Fund of Shenzhen Science and Technology
    .

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