A Divergent Synthesis to Generate Targeted Libraries of Inhibitors for Endo-N-Acetylglucosaminidases

Peer reviewed: 
Yes, item is peer reviewed.
Scholarly level: 
Faculty/Staff
Final version published as: 

Seo, I. K., Woo, E. H., Cecioni, S., & Vocadlo, D. J. (2017). A divergent synthesis to generate targeted libraries of inhibitors for endo-N-acetylglucosaminidases. Canadian Journal of Chemistry, 96(2), 248–254. https://doi.org/10.1139/cjc-2017-0461

Date created: 
2017-12-18
Identifier: 
DOI: doi.org/10.1139/cjc-2017-0461
Keywords: 
Enzyme inhibitor
Glucosaminidase
Substrate-assisted catalysis
Thiazoline
Abstract: 

Cell active inhibitors of glycoside processing enzymes are valuable research tools that help us understand the physiological roles of this diverse class of enzymes. endo-N-Acetylglucosaminidases have gained increased attention for their important roles in both mammals and human pathogens; however, metabolically stable cell active inhibitors of these enzymes are lacking. Here, we describe a divergent synthetic strategy involving elaboration of a thiazoline core scaffold. We illustrate the potential of this approach by using the copper catalysed azide-alkyne click (CuAAC) reaction, in combination with a suitable catalyst to avoid poisoning by the thiazoline moiety, to generate a targeted panel of candidate inhibitors of endo-N-acetylglucosaminidases and chitinases

Language: 
English
Document type: 
Article
Rights: 
Rights remain with the authors.
File(s): 
Sponsor(s): 
Canadian Institutes of Health Research (CIHR)
Statistics: