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Asymmetric Michael Reaction Catalyzed by Mimicked Peptides

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Abstract

Peptides mimicked from active site of promiscuous aldo-ketoreductase were synthesized and tested as asymmetry catalysts in the Michael adduct reaction of aldehydes or ketones with nitroolefins to furnish the corresponding γ-nitroaldehydes, γ-nitroketones with up to 93 % yield, 99:1 dr and 71 % ee at room temperature and on eco-friendly solvents. Aspartic acid residue as second amino acid produced greater enantioselectivity.

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Authors and Affiliations

  1. Enzyme and Microbial Technology Research Centre, Universiti Putra Malaysia, 43400, Serdang, Selangor Darul Ehsan, Malaysia

    Saadi Bayat, Bimo Ario Tejo, Abu Bakar Salleh, Emilia Abdulmalek, Yahaya M. Normi & Mohd Basyaruddin Abdul Rahman

  2. Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, Serdang, Selangor Darul Ehsan, Malaysia

    Saadi Bayat, Bimo Ario Tejo, Emilia Abdulmalek & Mohd Basyaruddin Abdul Rahman

  3. Department of Biochemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor Darul Ehsan, Malaysia

    Abu Bakar Salleh

  4. Department of Cell and Molecular Biology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor Darul Ehsan, Malaysia

    Yahaya M. Normi

  5. Structural and Synthetic Biology Research Centre, Malaysia Genome Institute, Jalan Bangi, 43000, Kajang, Selangor Darul Ehsan, Malaysia

    Mohd Basyaruddin Abdul Rahman

Authors
  1. Saadi Bayat
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  2. Bimo Ario Tejo
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  3. Abu Bakar Salleh
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  4. Emilia Abdulmalek
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  5. Yahaya M. Normi
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  6. Mohd Basyaruddin Abdul Rahman
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Corresponding author

Correspondence to Mohd Basyaruddin Abdul Rahman.

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Bayat, S., Tejo, B.A., Salleh, A.B. et al. Asymmetric Michael Reaction Catalyzed by Mimicked Peptides. Catal Lett 144, 222–228 (2014). https://doi.org/10.1007/s10562-013-1156-6

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  • DOI: https://doi.org/10.1007/s10562-013-1156-6

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