PUGNAc
 | |
| Systematic (IUPAC) name | |
|---|---|
|
O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate | |
| Clinical data | |
| Pregnancy category |
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| Routes of administration | Oral |
| Identifiers | |
| CAS Number |
132489-69-1  |
| PubChem | CID 9576811 |
| Chemical data | |
| Formula | C15H19N3O7 |
| Molar mass | 353.33 |
| (verify) | |
PUGNAc is a 1,5-hydroximolactone, acting as an inhibitor of a variety of N-acetylhexosaminidases. It was long thought that increased levels of O-GlcNAc in human cells lead to Type II diabetes. O-GlcNAc levels were artificially raised with PUGNAc, which inhibits O-GlcNAcase, a beta-exo-N-acetylhexosaminidase which cleaves beta-O-linked-N-acetylglucosamine residues from glycoproteins. As a result of this inhibition, a type II diabetic phenotype was observed. Recent pharmacological studies using a more selective O-GlcNAcase inhibitor did not see this effect. However, genetic manipulation of O-GlcNAc levels is consistent with the effects observed by PUGNAc, namely insulin resistance upon elevation of O-GlcNAc levels.
Fictional references
PUGNAc was used by Michael Scofield in the television series Prison Break to keep his blood sugar level high to appear diabetic and to be resistant to insulin shots he was receiving from the infirmary. He wanted this to get unlimited access to the infirmary building. Michael Scofield used PUGNAc to follow through with his escape plan.