Jump to content

PUGNAc

From Wikipedia, the free encyclopedia
PUGNAc
Clinical data
Pregnancy
category
  • ?
Routes of
administration
Oral
Identifiers
  • O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H19N3O7
Molar mass353.331 g·mol−1
  (verify)

PUGNAc is a 1,5-hydroximolactone, acting as an inhibitor of a variety of N-acetylhexosaminidases.[1] 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.[2]

Fictional references

[edit]

PUGNAc was used by Michael Scofield in the television series Prison Break to keep his blood sugar level high to appear diabetic.[3]

References

[edit]
  1. ^ Cox NJ, Meister TR, Boyce M (March 2017). "Chemical biology of O-GlcNAc glycosylation". In Tan Z, Wang LX (eds.). Chemical biology of glycoproteins. United Kingdom: Royal Society of Chemistry. doi:10.1039/9781782623823-00094. ISBN 978-1-78801-122-8.
  2. ^ Cheng, Steven S.; Mody, Alison C.; Woo, Christina M. (2024-11-07). "Opportunities for Therapeutic Modulation of O-GlcNAc". Chemical Reviews. doi:10.1021/acs.chemrev.4c00417. ISSN 0009-2665.
  3. ^ Season 1, episode 1
[edit]