Pugnac

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate Proteins can be modified post-translationally by the addition of O-linked N-acetylglucosamine (O-GlcNAc). Nuclear cytoplasmic O-GlcNAcase and acetyltransferase (NCOAT) is a ?-N-acetylglucosaminidase that removes GlcNAc from O-glycosylated proteins. PUGNAc is a (phenylcarbamoyl)oxime analog of GlcNAc that reversibly inhibits NCOAT (Ki = 40-110 nM). It also less potently inhibits other hexosaminidases and exochitinases. (Z)-PUGNAc is a stereoisomer of PUGNAc that is a more potent inhibitor of NCOAT than the (E) isomer, both in vitro and in cells. CAS Number 132489-69-1 Product Name Pugnac IUPAC Name [(Z)-[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino] N-phenylcarbamate Molecular Formula C15H19N3O7 Molecular Weight 353.33 g/mol InChI InChI=1S/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1 InChI Key PBLNJFVQMUMOJY-JXZOILRNSA-N SMILES CC(=O)NC1C(C(C(OC1=NOC(=O)NC2=CC=CC=C2)CO)O)O Synonyms N-acetylglucosaminono-1,5-lactone O-(phenylcarbamoyl)oxime, NAc-LAPCO, O-(2-acetamido-2-deoxyglucopyranosylidene)amino N-phenylcarbamate, PUGNAC Canonical SMILES CC(=O)NC1C(C(C(OC1=NOC(=O)NC2=CC=CC=C2)CO)O)O Isomeric SMILES CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O/C1=NOC(=O)NC2=CC=CC=C2)CO)O)O CAS No: 132489-69-1 Synonyms: PugNAc(Z)-PugNAc MDL No: MFCD00145022 Chemical Formula: C15H19N3O7 Molecular Weight: 353.33 References: 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, p3392. Haltiwanger RS, et. al.,, J. Biol. Chem. 1988, 273, p3611