PUGNAc

Chemical compound
  • ?
Routes of
administrationOralIdentifiers
  • O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate
CAS Number
  • 132489-69-1 checkY
PubChem CID
  • 9576811
UNII
  • AWZ7VE64B6
CompTox Dashboard (EPA)
  • DTXSID101117756 Edit this at Wikidata
Chemical and physical dataFormulaC15H19N3O7Molar 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.

Fictional references

PUGNAc was used by Michael Scofield in the television series Prison Break to keep his blood sugar level high to appear diabetic.[2]

References

  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. ^ Season 1, episode 1
  • Research paper


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