Synthesis 2016; 48(22): 3917-3923
DOI: 10.1055/s-0035-1562781
paper
© Georg Thieme Verlag Stuttgart · New York

New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling

Anca G. Coman
a   University of Bucharest, Faculty of Chemistry, Department of Organic Chemistry, Biochemistry and Catalysis, 90 Panduri Street, 050663 Bucharest, Romania   Email: mihaela.matache@g.unibuc.ro
,
Codruta C. Paraschivescu
a   University of Bucharest, Faculty of Chemistry, Department of Organic Chemistry, Biochemistry and Catalysis, 90 Panduri Street, 050663 Bucharest, Romania   Email: mihaela.matache@g.unibuc.ro
,
Niculina D. Hadade
b   Faculty of Chemistry and Chemical Engineering, ‘Babeș-Bolyai’ University, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania
,
Andrei Juncu
c   Institute of Biochemistry of the Romanian Academy, 296 Splaiul Independetei Avenue, 060031 Bucharest, Romania
,
Ovidiu Vlaicu
c   Institute of Biochemistry of the Romanian Academy, 296 Splaiul Independetei Avenue, 060031 Bucharest, Romania
,
Costin-Ioan Popescu
c   Institute of Biochemistry of the Romanian Academy, 296 Splaiul Independetei Avenue, 060031 Bucharest, Romania
,
Mihaela Matache*
a   University of Bucharest, Faculty of Chemistry, Department of Organic Chemistry, Biochemistry and Catalysis, 90 Panduri Street, 050663 Bucharest, Romania   Email: mihaela.matache@g.unibuc.ro
› Author Affiliations
Further Information

Publication History

Received: 26 April 2016

Accepted after revision: 18 June 2016

Publication Date:
29 July 2016 (online)


§ These authors contributed equally to this work

Abstract

Peptidyl-acyloxymethyl ketones (AOMKs) belong to a class of selective, irreversible inhibitors (activity-based probes) widely used as chemical tools of investigating proteins, for example, in activity-based protein profiling. The synthesis of the AOMKs has always been challenging and current methodologies involve both solution and solid-phase synthesis. Herein, the synthesis of a new scaffold useful for the preparation of peptidyl-AOMKs is reported and it is demonstrated that the new synthetic probes bearing a 4-functionalized 2,6-dimethylbenzoate efficiently inhibit cysteine proteases like cathepsin B.

Supporting Information

 
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