Issue 21, 2016
From the journal:

Chemical Communications

Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib†

Gerjan de Bruin,‡a   Elliot D. Mock,‡a   Sascha Hoogendoorn,a   Adrianus M. C. H. van den Nieuwendijk,a   Jaroslaw Mazurek,b   Gijsbert A. van der Marel,a   Bogdan I. Floreaa  and  Herman S. Overkleeft*a  

* Corresponding authors

a Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands
E-mail: h.s.overkleeft@lic.leidenuniv.nl

b Crystallics B.V., Meibergdreef 31, 1105 AZ Amsterdam, The Netherlands

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

DOI
https://doi.org/10.1039/C6CC01156J
Article type
Communication
Submitted
04 Feb 2016
Accepted
16 Feb 2016
First published
16 Feb 2016

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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