O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate
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1. Khidekel N, Ficarro SB, Clark PM, Bryan MC, Swaney DL, Rexach JE, Sun YE, Coon JJ, Peters EC, Hsieh-Wilson LC,, Nature Chemicl Biology, 2007, 3, p339
2. Haltiwanger RS, et. al.,, J. Biol. Chem. 1988, 273, p3611
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PUGNAcThe enzyme inhibitor O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate is more commonly referred to as PUGNAc.
PUGNAc is a potent inhibitor of the enzyme O-GlcNAcase which cleaves O-linked
2-acetamido-2-deoxy-beta-D-glucopyranoside (abbreviated as O-linked N-acetylglucosamine or O-GlcNAc) from serine and threonine residues of post-translationally modified proteins. O-GlcNAc is a common post-translational modification of proteins in the nucleus and cytoplasm and is believed to be dynamically regulated in similar fashion to protein phosphorylation.1
PUGNAc is also an inhibitor of the functionally related enzyme β-hexosaminidase exhibiting little selectivity between the two.2 The Z oxime stereoisomer (shown above) has been identified as a significantly more potent inhibitor of O-GlcNAcase than the E isomer in both in vitro and intact cellular experiments. 3 In rats, PUGNAc has been shown to provide a protective effect on cardiac function after trauma-haemorrhage, mediated through an increase in levels of protein O-GlcNAc.4
1. RS Haltiwanger et al, J. Biol. Chem., 1998, 273, 3611.
2. GE Whitworth et al, J. Am. Chem. Soc., 2007, 129, 635.
3. M Perreira et al, Bioorg. Med. Chem., 2006, 14, 837 and Bioorg. Med. Chem., 2006, 14, 7359.
4. L Zou et al, Shock, 2007, 27, 402.