Aswad, Muhammad and Chiba, Junya and Tomohiro, Takenori and Hatanaka, Yasumaru (2017) Simple Synthesis of Sulfonyl Amidine-Containing Glucosidase Inhibitors by a Chemoselective Coupling Reaction Between D-Gluconothiolactam and Sulfonyl Azides. International Research Journal of Pure and Applied Chemistry, 14 (2). pp. 1-8. ISSN 22313443
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Abstract
In this report, we describe a simple synthesis of gluconoamidinylsulfones as a new class of potential inhibitors toward glycan processing enzymes. Gluconoamidinylsulfones have a glucose-based sulfonyl amidine skeleton, thus would form a distorted half-chair conformation with positive charge, which is analogous to transition state in the enzymatic process. A chemoselective coupling reaction between thioamide and sulfonyl azide enabled one-step synthesis of the iminosugar derivatives from commercially available D-gluconothiolactam in a protection-free manner. The phenyl-substituted gluconoamidinylsulfone displayed high inhibitory ability toward a- and b-glucosidases with Ki values of 13.9 and 8.2 mM, respectively, resulting that gluconoamidinylsulfones would be expected to entry in a new class of promising potential inhibitors toward various glycan-processing enzymes.
Item Type: | Article |
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Subjects: | Bengali Archive > Chemical Science |
Depositing User: | Unnamed user with email support@bengaliarchive.com |
Date Deposited: | 13 May 2023 07:29 |
Last Modified: | 23 Sep 2024 04:42 |
URI: | http://science.archiveopenbook.com/id/eprint/1015 |