Chemical Science p. 2782 - 2789 (2015)
Update date:2022-08-10
Topics:
Jiang, Jianbing
Kallemeijn, Wouter W.
Wright, Daniel W.
Van Den Nieuwendijk, Adrianus M. C. H.
Rohde, Veronica Coco
Folch, Elisa Colomina
Van Den Elst, Hans
Florea, Bogdan I.
Scheij, Saskia
Donker-Koopman, Wilma E.
Verhoek, Marri
Li, Nan
Schürmann, Martin
Mink, Daniel
Boot, Rolf G.
Codée, Jeroen D. C.
Van Der Marel, Gijsbert A.
Davies, Gideon J.
Aerts, Johannes M. F. G.
Overkleeft, Herman S.
GH29 α-L-fucosidases catalyze the hydrolysis of α-L-fucosidic linkages. Deficiency in human lysosomal α-L-fucosidase (FUCA1) leads to the recessively inherited disorder, fucosidosis. Herein we describe the development of fucopyranose-configured cyclophellitol aziridines as activity-based probes (ABPs) for selective in vitro and in vivo labeling of GH29 α-L-fucosidases from bacteria, mice and man. Crystallographic analysis on bacterial α-L-fucosidase confirms that the ABPs act by covalent modification of the active site nucleophile. Competitive activity-based protein profiling identified l-fuconojirimycin as the single GH29 α-L-fucosidase inhibitor from eight configurational isomers.
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