Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines

Sybrin P. Schröder; Jasper W. van de Sande; Wouter W. Kallemeijn; Chi-Lin Kuo; Marta Artola; Eva J. van Rooden; Jianbing Jiang; Thomas J. M. Beenakker; Bogdan I. Florea; Wendy A. Offen; Gideon J. Davies; Adriaan J. Minnaard; Johannes M. F. G. Aerts; Jeroen D. C. Codée; Gijsbert A. van der Marel; Herman S. Overkleeft

doi:10.1039/C7CC07730K

Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines†

Sybrin P. Schröder,

^a Jasper W. van de Sande,^a Wouter W. Kallemeijn,^b Chi-Lin Kuo,^b Marta Artola,^a Eva J. van Rooden,^a Jianbing Jiang,^a Thomas J. M. Beenakker,^a Bogdan I. Florea,^a Wendy A. Offen,^c Gideon J. Davies,

^c Adriaan J. Minnaard,

^d Johannes M. F. G. Aerts,^b Jeroen D. C. Codée,^a Gijsbert A. van der Marel^a and Herman S. Overkleeft

*^a

Author affiliations

* Corresponding authors

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

^b Department of Medical Biochemistry, Leiden Institute of Chemistry, The Netherlands

^c Department of Chemistry, York Structural Biology Laboratory, The University of York, Heslington, York, UK

^d Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands

Abstract

Activity-based protein profiling has emerged as a powerful tool for visualizing glycosidases in complex biological samples. Several configurational cyclophellitol isomers have been shown to display high selectivity as probes for glycosidases processing substrates featuring the same configuration. Here, a set of deoxygenated cyclophellitols are presented which enable inter-class profiling of β-glucosidases and β-galactosidases.

Chemical Communications

Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines†

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Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines

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