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

DOI: 10.1039/C7CC07730K DOI Help

Authors: Sybrin P. Schröder (Leiden Institute of Chemistry, Leiden University) , Jasper W. Van De Sande (Leiden Institute of Chemistry, Leiden University) , Wouter W. Kallemeijn (Leiden Institute of Chemistry, Leiden University) , Chi-lin Kuo (Leiden Institute of Chemistry, Leiden University) , Marta Artola (Leiden Institute of Chemistry, Leiden University) , Eva J. Van Rooden (Leiden Institute of Chemistry, Leiden University) , Jianbing Jiang (Leiden Institute of Chemistry, Leiden University) , Thomas J. M. Beenakker (Leiden Institute of Chemistry, Leiden University) , Bogdan I. Florea (Leiden Institute of Chemistry, Leiden University) , Wendy Offen (The University of York) , Gideon Davies (The University of York) , Adriaan J. Minnaard (Stratingh Institute for Chemistry, University of Groningen) , Johannes M. F. G. Aerts (Leiden Institute of Chemistry, Leiden University) , Jeroen D. C. Codée (Leiden Institute of Chemistry, Leiden University) , Gijsbert A. Van Der Marel (Leiden Institute of Chemistry, Leiden University) , Herman S. Overkleeft (Leiden Institute of Chemistry, Leiden University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemical Communications , VOL 3

State: Published (Approved)
Published: November 2017
Diamond Proposal Number(s): 9948

Open Access Open Access

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.

Subject Areas: Chemistry, Biology and Bio-materials


Instruments: I02-Macromolecular Crystallography

Documents:
C7CC07730K.pdf