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A Convenient Approach to Stereoisomeric Iminocyclitols: Generation of Potent Brain-Permeable OGA Inhibitors.
- Source :
- Angewandte Chemie International Edition; 12/14/2015, Vol. 54 Issue 51, p15429-15433, 5p, 2 Color Photographs, 4 Diagrams
- Publication Year :
- 2015
-
Abstract
- Pyrrolidine-based iminocyclitols are a promising class of glycosidase inhibitors. Reported herein is a convenient epimerization strategy that provides direct access to a range of stereoisomeric iminocyclitol inhibitors of O-GlcNAcase (OGA), the enzyme responsible for catalyzing removal of OGlcNAc from nucleocytoplasmic proteins. Structural details regarding the binding of these inhibitors to a bacterial homologue of OGA reveal the basis for potency. These compounds are orally available and permeate into rodent brain to increase O-GlcNAc, and should prove useful tools for studying the role of OGA in health and disease. [ABSTRACT FROM AUTHOR]
- Subjects :
- PYRROLIDINE
HETEROCYCLIC compounds
STEREOISOMERS
ISOMERISM
RODENTS
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 54
- Issue :
- 51
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 111665807
- Full Text :
- https://doi.org/10.1002/anie.201507985