187146-99-2

Basic information

• Product Name: p-Aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• Synonyms: p-Aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS NO: 187146-99-2
• Molecular Weight: 439.419
• Mol File: 187146-99-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: p-Aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-Aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(187146-99-2)
• EPA Substance Registry System: p-Aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(187146-99-2)

Safety Data

• Hazardous Substances Data: 187146-99-2(Hazardous Substances Data)

Upstream product

• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 100-02-7 4-nitro-phenol 
• 13242-53-0 acetobromomannose 
• 83-87-4 D-Mannose pentaacetate 
• 10357-27-4 4-nitrophenyl-α-D-mannopyranoside 
• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 

Downstream Products

• 34213-86-0 p-aminophenyl-α-D-mannopyranoside 
• 187147-01-9 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-acetylsulfanyl-propionylamino)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 187147-02-0 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-mercapto-propionylamino)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 187147-07-5 p-acrylamidophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 187147-00-8 p-acrylamidophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Relevant articles and documents

Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling

The development of new bio-orthogonal ligation methods for the conjugation of native proteins is of particular importance in the field of chemical biology and biotherapies. In this work, we developed a traceless electrochemical method for protein bioconju

Carbohydrate mediated drug delivery: Synthesis and characterization of new lipid-conjugates

A new synthetic methodology for cationic glycolipids using p-aminophenyl-α-d-mannopyranoside (PAPM) and p-aminophenyl-α-d-galactopyranoside (PAPG) with spacer in between the quaternary nitrogen atom and the sugar unit is developed. In addition, a new clas

Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry

Carbohydrates are extremely important biomolecules and their immobilization onto solid surfaces is of interest for the development of new biomimetic materials and of new methods for understanding processes in glycobiology. We have developed an efficient surface modification methodology for the functionalization of a range of materials with biologically active carbohydrates based on aryldiazonium chemistry. We describe the synthesis and characterization of carbohydrate reagents, which were subsequently employed for the one-step, solution-based modification of carbon, metals, and alloys with monosaccharides. We used a combination of spectroscopic and nanogravimetric methods to characterize the structure of the carbohydrate layers; we report an average surface coverage of 7.8 × 10-10 mol cm-2 under our experimental conditions. Concanavalin A, a mannose-binding lectin, and Peanut Agglutinin, a galactose-binding lectin, were found to bind from solution to their respective monosaccharide binding partners immobilized at the surface. This result suggests that the spontaneous chemisorption of aryldiazonium monosaccharide precursors leads to the formation of monosaccharide layers that retain the biological recognition specificity of the parent carbohydrate molecule. Finally, we carried out measurements using fluorescently labeled Bovine Serum Albumin (BSA) and found that these carbohydrate coatings reduce unspecific adsorption of this protein at carbon surfaces. These results suggest that aryldiazonium-derived carbohydrate coatings may offer a promising strategy for preventing undesirable protein accumulation onto surfaces.