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Updated: Aug 22, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile
Ganesh Shrestha1, Matteo Panza1, Yashapal Singh1
1Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.
Abstract:
While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides.
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