Article · Wikipedia archive · Last revised Aug 8, 2026

PUGNAc

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.

Last revised
Aug 8, 2026
Read time
≈ 1 min
Length
260 w
Citations
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Source
Wikipedia ↗
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
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H19N3O7
Molar mass353.331 g·mol−1
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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

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

References

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. pp. 94–149. doi:10.1039/9781782623823-00094. ISBN 978-1-78801-122-8.
  2. Cheng SS, Mody AC, Woo CM (2024-11-07). "Opportunities for Therapeutic Modulation of O-GlcNAc". Chemical Reviews. 124 (22): 12918–13019. doi:10.1021/acs.chemrev.4c00417. ISSN 0009-2665. PMID 39509538.
  3. Season 1, episode 1
Further reading

Further reading