Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 14, Issue 3, Pages 837-846Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2005.09.013
Keywords
PUGNAc; O-GlcNAcase; oxime stereochemistry
Funding
- Intramural NIH HHS [Z01 DK070005-04] Funding Source: Medline
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The potent O-GlcNAcase inhibitor PUGNAc was synthesized and two isomers based on the E and Z stereochemistry of the oxime moiety were separated, defined, and tested for activity. Several lines of evidence were examined in an effort to define the correct stereochemical assignments of each form of PUGNAc. The ability of the Z stereoisomer to undergo the Beckmann rearrangement was ultimately the most definitive proof. It was determined via both in vitro and intact cell experiments that the Z form of PUGNAc was vastly more potent an inhibitor of O-GIcNAcase than the E form. (c) 2005 Elsevier Ltd. All rights reserved.
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