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Publication 18  


  1. 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, H. S. Overkleeft
    Chem. Commun. 2016, 52, 4064-4067

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.

DOI: 10.1039/C6CC01156J