PUGNAc

Last updated

PUGNAc
Pugnac.png
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
Formula C15H19N3O7
Molar mass 353.331 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]

Contents

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

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


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