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Challenges and recent advancements in the synthesis of α,α-disubstituted α-amino acids

Author

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  • Yu Zhang

    (Shanghai University of Traditional Chinese Medicine
    University of Antwerp)

  • Jaro Vanderghinste

    (University of Antwerp)

  • Jinxin Wang

    (Shanghai University of Traditional Chinese Medicine)

  • Shoubhik Das

    (University of Antwerp
    University of Bayreuth)

Abstract

α,α-Disubstituted α-amino acids (α-AAs) have improved properties compared to other types of amino acids. They serve as modifiers of peptide conformation and as precursors of bioactive compounds. Therefore, it has been a long-standing goal to construct this highly valuable scaffold efficiently in organic synthesis and drug discovery. However, access to α,α-disubstituted α-AAs is highly challenging and largely unexplored due to their steric constraints. To overcome these, remarkable advances have been made in the last decades. Emerging strategies such as synergistic enantioselective catalysis, visible-light-mediated photocatalysis, metal-free methodologies and CO2 fixation offer new avenues to access the challenging synthesis of α,α-disubstituted α-AAs and continuously bring additional contributions to this field. This review article aims to provide an overview of the recent advancements since 2015 and discuss existing challenges for the synthesis of α,α-disubstituted α-AAs and their derivatives.

Suggested Citation

  • Yu Zhang & Jaro Vanderghinste & Jinxin Wang & Shoubhik Das, 2024. "Challenges and recent advancements in the synthesis of α,α-disubstituted α-amino acids," Nature Communications, Nature, vol. 15(1), pages 1-18, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-45790-2
    DOI: 10.1038/s41467-024-45790-2
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    References listed on IDEAS

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    1. Qiang Liu & Lipeng Wu & Ralf Jackstell & Matthias Beller, 2015. "Using carbon dioxide as a building block in organic synthesis," Nature Communications, Nature, vol. 6(1), pages 1-15, May.
    2. Daniel J. Leonard & John W. Ward & Jonathan Clayden, 2018. "Asymmetric α-arylation of amino acids," Nature, Nature, vol. 562(7725), pages 105-109, October.
    3. Qiang Fu & Zhi-Yu Bo & Jian-Heng Ye & Tao Ju & He Huang & Li-Li Liao & Da-Gang Yu, 2019. "Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
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