Pugnac

Base Information

• Chemical Name: Pugnac
• CAS No.: 132489-69-1
• Molecular Formula: C15H19 N3 O7
• Molecular Weight: 353.332
• Hs Code.: 29329990
• UNII: AWZ7VE64B6
• DSSTox Substance ID: DTXSID101117756
• Wikipedia: PUGNAc
• Pharos Ligand ID: MMH389DPAGMN
• ChEMBL ID: CHEMBL404482
• Mol file: 132489-69-1.mol

Synonyms:N-acetylglucosaminono-1,5-lactone O-(phenylcarbamoyl)oxime;NAc-LAPCO;O-(2-acetamido-2-deoxyglucopyranosylidene)amino N-phenylcarbamate;PUGNAC

Chemical Property of Pugnac

Chemical Property:

• Melting Point: 172-175°C
• Boiling Point: °Cat760mmHg
• PKA: 11.85±0.70(Predicted)
• Flash Point: °C
• PSA: 149.71000
• Density: 1.53g/cm³
• LogP: -0.36990
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 35 mg/ml)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 353.12229995
• Heavy Atom Count: 25
• Complexity: 507

Purity/Quality:

98%, ^*data from raw suppliers

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)aminoN-Phenylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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=N\OC(=O)NC2=CC=CC=C2)CO)O)O
• Description: 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 β-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.
• Uses: An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B O-(2-acetamido-2deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate (PUGNAc) has been used to evaluate the effects of silibinin on O-GlcNAc levels of glycoproteins in Adult Retinal Pigment Epithelial-19 (ARPE-19) cells. It has also been used as a component of the HEPES lysis buffer for rat brain samples.

Technology Process of Pugnac

There total 7 articles about Pugnac which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate (872611-17-1) → O-(2-acetamido-2-deoxy-D-glucopyranosylidene)-amino N-phenylcarbamate (132489-69-1,132063-05-9,872611-16-0)

Guidance literature:

With ammonia; water; In methanol; at -10 ℃; for 12h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<114::AID-HLCA114>3.0.CO;2-9

Reference yield: 61.0%

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate (132063-04-8) → O-(2-acetamido-2-deoxy-D-glucopyranosylidene) amino-N-phenylcarbamate (132489-69-1,132063-05-9,872611-16-0)

Guidance literature:

With methanol; ammonia; for 4h;

DOI:10.1002/hlca.19900730714

Reference yield:

phenyl isocyanate (103-71-9) → O-(2-acetamido-2-deoxy-D-glucopyranosylidene)-amino N-phenylcarbamate (132489-69-1,132063-05-9,872611-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Et₃N / tetrahydrofuran / 3 h / 20 °C

2: 73 percent / NH₃; water / methanol / 12 h / -10 °C

With ammonia; water; triethylamine; In tetrahydrofuran; methanol; 1: Addition / 2: Deacetylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<114::AID-HLCA114>3.0.CO;2-9

upstream raw materials:

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(Z)-hydroxyimino]-tetrahydro-pyran-4-yl ester

C₁₆H₂₂N₂O₁₀

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

Downstream raw materials:

N-phenylcarbamic acid