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Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

Back to (non-)Basics: An Update on Neutral and Charge-Balanced Glycosidase Inhibitors

Author(s): Michela I. Simone*, Laura J. Mares, Clothilde A. Eveleens, Adam McCluskey, Brighid B. Pappin, Milton J. Kiefel and Todd A. Houston*

Volume 18, Issue 10, 2018

Page: [812 - 827] Pages: 16

DOI: 10.2174/1389557517666171002161325

Price: $65

Abstract

Glycosidases have important anti-cancer, anti-viral and anti-diabetic properties. This review covers the literature in the past 15 years since our initial review in this journal on “neutral” glycosidase inhibitors lacking a basic nitrogen found in iminosugars and azasugars or inhibitors that are neutral by virtue of being “charge-balanced” (zwitterionic). These structurally diverse inhibitors include lactones, lactams, epoxides such as cyclophellitol, and sulfonium ion derivatives of the natural product salacinol. Synthetic efforts toward cyclophillitol, salicinol and derivatives are also highlighted. Importantly, certain metals can inhibit glycosidases and care must be taken to remove residual catalysts from synthetic material to be tested against these enzymes.

Keywords: Cadmium, computational, copper, cyclophellitol, deoxynojirimycin, diabetes, electrophilic, epoxide, fucosidase, galactosidase, glucocerebroside, glucosidase, glycal, homology, hydantocidin, iminosugar, lactam, lactone, mannosidase, metal complex, modeling, molybdenum, natural product, palladium, salacinol, sialidase, silver, transition-state mimic, vanadium, X-ray crystallography, zinc.

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