Literature DB >> 22932951

Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes.

Marthe T C Walvoort1, Wouter W Kallemeijn, Lianne I Willems, Martin D Witte, Johannes M F G Aerts, Gijsbert A van der Marel, Jeroen D C Codée, Herman S Overkleeft.   

Abstract

The potency of 2-deoxy-2-fluoroglycosides in activity-based profiling of human acid β-glucosidase is drastically improved by introducing an N-phenyl trifluoroacetimidate leaving group at the anomeric center. Protonation by the general acid-base catalyst in the active site turned out to be a prerequisite, making the imidate probe a genuine mechanism-based glycosidase inactivator.

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Year:  2012        PMID: 22932951     DOI: 10.1039/c2cc35653h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

1.  Suite of activity-based probes for cellulose-degrading enzymes.

Authors:  Lacie M Chauvigné-Hines; Lindsey N Anderson; Holly M Weaver; Joseph N Brown; Phillip K Koech; Carrie D Nicora; Beth A Hofstad; Richard D Smith; Michael J Wilkins; Stephen J Callister; Aaron T Wright
Journal:  J Am Chem Soc       Date:  2012-12-06       Impact factor: 15.419

2.  Stabilization of Glucocerebrosidase by Active Site Occupancy.

Authors:  Fredj Ben Bdira; Wouter W Kallemeijn; Saskia V Oussoren; Saskia Scheij; Boris Bleijlevens; Bogdan I Florea; Cindy P A A van Roomen; Roelof Ottenhoff; Marielle J F M van Kooten; Marthe T C Walvoort; Martin D Witte; Rolf G Boot; Marcellus Ubbink; Herman S Overkleeft; Johannes M F G Aerts
Journal:  ACS Chem Biol       Date:  2017-05-22       Impact factor: 5.100

3.  Novel approaches in function-driven single-cell genomics.

Authors:  Devin F R Doud; Tanja Woyke
Journal:  FEMS Microbiol Rev       Date:  2017-07-01       Impact factor: 16.408

  3 in total

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