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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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Article information


Submitted
04 Feb 2016
Accepted
16 Feb 2016
First published
16 Feb 2016

Chem. Commun., 2016,52, 4064-4067
Article type
Communication

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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