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Issue 21, 2016
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Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib

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Abstract

The incorporation of adamantylalanine and carboranylalanine at the P2 site of bortezomib is well tolerated and provided potent cell permeable proteasome inhibitors with increased off-rates compared to bortezomib. Adamantylalanine and carboranylalanine were synthesized enantioselectively by an asymmetric Strecker reaction on Ellmans tert-butyl sulfinimines.

Graphical abstract: Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib

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Publication details

The article was received on 04 Feb 2016, accepted on 16 Feb 2016 and first published on 16 Feb 2016


Article type: Communication
DOI: 10.1039/C6CC01156J
Citation: Chem. Commun., 2016,52, 4064-4067
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    Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib

    G. de Bruin, E. D. Mock, S. Hoogendoorn, A. M. C. H. van den Nieuwendijk, J. Mazurek, G. A. van der Marel, B. I. Florea and H. S. Overkleeft, Chem. Commun., 2016, 52, 4064
    DOI: 10.1039/C6CC01156J

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