2872-66-4

Basic information

• Product Name: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE
• Synonyms: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE;P-NITROPHENYL-BETA-D-GALACTOPYRANOSIDE TETRAACETATE;Nsc89591
• CAS NO: 2872-66-4
• Molecular Formula: C₂₀H₂₃NO₁₂
• Molecular Weight: 469.3961
• Product Categories: Carbohydrates & Derivatives
• Mol File: 2872-66-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 144-145 °C
• Boiling Point: 559.3°Cat760mmHg
• Flash Point: 207.1°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 1.53E-12mmHg at 25°C
• Refractive Index: 1.54
• Solubility: Chloroform
• CAS DataBase Reference: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE(2872-66-4)
• EPA Substance Registry System: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE(2872-66-4)

Safety Data

• Hazardous Substances Data: 2872-66-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

p-Nitrophenyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside (cas# 2872-66-4) is a compound useful in organic synthesis.

InChI:InChI=1/C20H23NO12/c1-10(22)28-9-16-17(29-11(2)23)18(30-12(3)24)19(31-13(4)25)20(33-16)32-15-7-5-14(6-8-15)21(26)27/h5-8,16-20H,9H2,1-4H3/t16-,17+,18+,19-,20-/m1/s1

Upstream product

• 100-02-7 4-nitro-phenol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 108-24-7 acetic anhydride 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 1420786-80-6 C₂₉H₂₈O₁₁ 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 25878-60-8 D-galactose pentaacetate 
• 10257-28-0 D-Galactose 
• 824-78-2 4-nitrophenol sodium salt 
• 572-09-8 acetobromogalactose 

Downstream Products

• 1427462-40-5 5-(-N-(p-O-(2,3,4,6-tetra-O-acetyl-β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 1427462-44-9 5-(-N-(p-O-(β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 5094-33-7 p-aminophenyl β-D-galactopyranoside 

Relevant articles and documents

Nitrogen-containing aromatic ring derivative containing galactose and application thereof

The invention belongs to the technical field of medicines, and relates to a nitrogen-containing aromatic ring derivative containing galactose, application thereof and a pharmaceutical composition containing the compound. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in prevention or treatment of tumors, inflammatory diseases, autoimmune diseases and other diseases, especially tumors.

Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan

β-D-Galactofuranose (Galf) is a component of polysaccharides and glycoconjugates. There are few reports about the involvement of galactofuranosyltransferases and galactofuranosidases (Galf-ases) in the synthesis and degradation of galactofuranose-containing glycans. The cell walls of filamentous fungi in the genus Aspergillus include galactofuranose-containing polysaccharides and glycoconjugates, such as O-glycans, N-glycans, and fungal-type galactomannan, which are important for cell wall integrity. In this study, we investigated the synthesis of p-nitrophenyl β-D-galactofuranoside and its disaccharides by chemo-enzymatic methods including use of galactosidase. The key step was selective removal of the concomitant pyranoside by enzymatic hydrolysis to purify p-nitrophenyl β-D-galactofuranoside, a promising substrate for β-D-galactofuranosidase from Streptomyces species.

Development of Pseudomonas aeruginosa Lectin LecA Inhibitor by using Bivalent Galactosides Supported on Polyproline Peptide Scaffolds

LecA is a galactose-binding tetrameric lectin from Pseudomonas aeruginosa involved in infection and biofilm formation. The emergent antibiotic resistance of P. aeruginosa has made LecA a promising pharmaceutical target to treat such infections. To develop LecA inhibitors, we exploit the unique helical structure of polyproline peptides to create a scaffold that controls the galactoside positions to fit their binding sites on LecA. With a modular scaffold design, both the galactoside ligands and the inter-ligand distance can be altered conveniently. We prepared scaffolds with spacings of 9, 18, 27, and 36 ? for ligand conjugation and found that glycopeptides with galactosides ligands three helical turns (27 ?) apart best fit LecA. In addition, we tested different galactose derivatives on the selected scaffold (27 ?) to improve the binding avidity to LecA. The results validate a new multivalent scaffold design and provide useful information for LecA inhibitor development.