PUGNAc

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PUGNAc

Clinical data
Pregnancy category	?
Routes of administration	Oral
Identifiers
IUPAC name O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate
CAS Number	132489-69-1 Y
PubChem CID	9576811
UNII	AWZ7VE64B6
ChEBI	CHEBI:44601
CompTox Dashboard (EPA)	DTXSID101117756
Chemical and physical data
Formula	C15H19N3O7
Molar mass	353.331 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]

• Vosseller K, Wells L, Lane MD, Hart GW (April 2002). "Elevated nucleocytoplasmic glycosylation by O-GlcNAc results in insulin resistance associated with defects in Akt activation in 3T3-L1 adipocytes". Proceedings of the National Academy of Sciences of the United States of America. 99 (8): 5313–8. Bibcode:2002PNAS...99.5313V. doi:10.1073/pnas.072072399. PMC 122766. PMID 11959983.

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