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α-Boryl Isocyanides Enable Facile Preparation of Bioactive Boropeptides†

Authors

  • Adam Zajdlik,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S3H6 (Canada)
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  • Dr. Zezhou Wang,

    1. Ontario Cancer Institute, Princess Margaret Cancer Center, University Health Network, Toronto, ON M5G2 M9 (Canada)
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  • Jennifer L. Hickey,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S3H6 (Canada)
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  • Dr. Ahmed Aman,

    1. Ontario Institute for Cancer Research, MaRS Centre, South Tower, 101 College St. S., Suite 800 Toronto, ON M5G0 A3 (Canada)
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  • Dr. Aaron D. Schimmer,

    1. Ontario Cancer Institute, Princess Margaret Cancer Center, University Health Network, Toronto, ON M5G2 M9 (Canada)
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  • Prof. Dr. Andrei K. Yudin

    Corresponding author
    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S3H6 (Canada)
    • Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S3H6 (Canada)
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  • †

    We would like to thank the Natural Science and Engineering Research Council (NSERC) and Canadian Institutes of Health Research (CIHR) for financial support.

Abstract

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Entry to bioactive boropeptides: MIDA-containing α-boryl isocyanides are isolable molecules which allow one-step access to boroalkyl-functionalized heterocycles as well as biologically active boropeptides through a multicomponent approach. Among these derivatives are 6-boromorpholinones, novel borocycles with nanomolar IC50 values for 20S proteasome inhibition. MIDA=N-methyliminodiacetyl.

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Article Information

DOI

10.1002/anie.201302818

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Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • boron;
  • inhibitors;
  • isocyanides;
  • multicomponent reactions;
  • peptides

Publication History

  • Issue online:
  • Version of record online:
  • Manuscript Revised:
  • Manuscript Received:

Funded by

  • Natural Science and Engineering Research Council (NSERC)
  • Canadian Institutes of Health Research (CIHR)

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