34213-86-0

Basic information

• Product Name: P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE
• Synonyms: 4-AMINOPHENYL A-D-MANNOPYRANOSIDE;4-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE;P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE;P-AMINOPHENYL-A-D-MANNOPYRANOSIDECRYSTAL LINE;4-aminophenyl α-d-mannopyranoside;4-aminophenylmannoside;(2R,3S,4S,5S,6R)-2-(4-aminophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol;(2R,3S,4S,5S,6R)-2-(4-aminophenoxy)-6-methylol-tetrahydropyran-3,4,5-triol
• CAS NO: 34213-86-0
• Molecular Formula: C₁₂H₁₇NO₆
• Molecular Weight: 271.27
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Carbohydrates;Carbohydrates A to;Carbohydrates A-CBiochemicals and Reagents;Monosaccharide;Amines;Aromatics
• Mol File: 34213-86-0.mol

Chemical Properties

• Melting Point: 165-166°C
• Boiling Point: 555.9°Cat760mmHg
• Flash Point: 290°C
• Appearance: /
• Density: 1.517g/cm³
• Vapor Pressure: 3.43E-13mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• PKA: 12.93±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE(34213-86-0)
• EPA Substance Registry System: P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE(34213-86-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 34213-86-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE is used as a pharmaceutical compound for its potential therapeutic applications. Its unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Drug Delivery Systems:
P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE is used as a component in drug delivery systems to increase the uptake rate of liposomes. Its chemical properties enable it to enhance the efficiency of drug delivery, potentially improving the effectiveness of treatments.
Used in Research and Development:
P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE is used as a research compound for studying its interactions with various biological molecules and systems. This can lead to a better understanding of its potential applications and the development of new technologies or治疗方法 (治疗方法).
Used in Chemical Synthesis:
P-AMINOPHENYL ALPHA-D-MANNOPYRANOSIDE is used as a starting material or intermediate in the synthesis of other complex organic compounds. Its unique structure can be modified or used as a building block to create new molecules with specific properties and applications.

InChI:InChI=1/C12H17NO6/c13-6-1-3-7(4-2-6)18-12-11(17)10(16)9(15)8(5-14)19-12/h1-4,8-12,14-17H,5,13H2/t8-,9-,10+,11+,12+/m1/s1

Upstream product

• 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 
• 100-02-7 4-nitro-phenol 
• 83-87-4 D-Mannose pentaacetate 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 187146-99-2 p-Aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 7296-15-3 alpha-D-mannopyranoside 

Downstream Products

• 74590-39-9 p-(dimethylamino)phenyl α-D-mannopyranoside 
• 96345-79-8 [p-isothiocyanato]-phenyl α-D-mannopyranoside 
• 246855-92-5 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide 
• 51368-18-4 p-azidophenyl-α-D-mannopyranoside 
• 186390-49-8 4-Benzamidophenyl-α-D-mannopyranoside 
• 916849-16-6 3-ethoxy-4-[[4-(α-D-mannopyranosyloxy)phenyl]amino]-3-cyclobutene-1,2-dione 
• 1425814-80-7 C₂₈H₃₉ClN₂O₁₀ 
• 1417341-50-4 {N-[4-(α-D-mannopyranosyloxy)phenyl]-N’-[(2‘-tert-butyloxycarbonylamido)ethyl]}squaric acid diamide 
• 1417341-51-5 p-[((2-aminoethylamino)-2,3-dioxocyclobut-1-enyl)amino]phenyl α-D-mannopyranoside 

Relevant articles and documents

Glycodendrimer synthesis without using protecting groups

Oligoantennary neoglycoconjugates can act as powerful inhibitors of carbohydrate-protein interactions and thus serve as antiadhesives in carbohydrate-based adhesion systems. They were obtained by a procedure that doesn't require protecting groups. Various unprotected NCS-functionalized saccharides were coupled with oligoamines in aqueous solution. This versatile method is generally applicable to the synthesis of thiourea-bridged glycodendrimers.

Nickel-charcoal as a catalyst for the synthesis of p-aminophenyl α-D-mannopyranoside and α-L-fucopyranoside

The p-aminophenyl glycosides have a variety of applications in the fields of protein, enzyme, and lectin purification1-5.A nickel-charcoal catalyst, prepared by reducing nickel(II) chloride hexahydrate with potassium borohydride in a solution o

Glycosyl-based united cell penetrating peptide-modified brain-targeted nano-liposome as well as preparation method and application thereof (by machine translation)

The invention relates to a glycosyl combined cell penetrating peptide-modified brain-targeted nano-liposome and a preparation method and application thereof, and belongs to the technical field of targeted drug delivery. The liposome comprises EPC, CHO, glycosyl modified polyethylene glycol phospholipid and cell penetrating peptide modified polyethylene glycol phospholipid with a certain molar ratio. By simultaneously modifying the glycosyl and the cell penetrating peptide on the surface of the nano liposome, the nano lipidosome has the capability of actively targeting brain and penetrating cell membranes. The drug carrier is used for a drug carrier, so that the carried medicines can efficiently and specifically target brain tissues and enter into brain cells to play a role. The in-vitro cell test and the in-vivo distribution experiment prove that the brain-targeted nano-liposome provided by the invention can reach the brain smoothly and accumulate in brain cells to exert efficacy. (by machine translation)

Brain-targeting nano liposome carrying positively charged polymer/miR-195 compound, and preparation method and application thereof

The invention relates to a brain-targeting nano liposome carrying a positively charged polymer/miR-195 compound, and a preparation method and application thereof, and belongs to the technical field oftargeting drug delivery. In order to improve stability of nucleic acid therapeutic drugs and penetration of blood brain barriers, the invention provides the brain targeting nano liposome carrying thepositively charged polymer/miR-195 compound, wherein the liposome containing a glycosyl modified polyethylene glycol phospholipid and a cell penetrating peptide modified polyethylene glycol phospholipid is taken as a drug carrier to envelop the positively charged polymer/miR-195 compound. According to the invention, stability of miR-195 is improved through the positively charged polymer and the drug carrier, and capability of the drug to target the brain and penetrate the cell membrane is improved through the glycosyl combined cell penetrating peptide modified brain targeting nano liposome, so that the carried drugs efficiently and specifically target brain tissues to treat Alzheimer's disease and vascular dementia, particularly cognitive dysfunction caused by Alzheimer's disease and cerebral ischemia.

Diazirine-functionalized mannosides for photoaffinity labeling: Trouble with FimH

Photoaffinity labeling is frequently employed for the investigation of ligand–receptor interactions in solution. We have employed an interdisciplinary methodology to achieve facile photolabeling of the lectin FimH, which is a bacterial protein, crucial fo

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.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating urinary tract infections.

Squaric Acid Monoamide Mannosides as Ligands for the Bacterial Lectin FimH: Covalent Inhibition or Not?

Bacteria use long proteinaceous appendages, called fimbriae or pili, to adhere to the surfaces of their host cells. Widely distributed among the Enterobacteriacae are type 1 fimbriae that mediate mannose-specific bacterial adhesion through the lectin FimH, located at the fimbrial tips. It is possible to design synthetic mannosides such that they show high affinity for FimH and can thus inhibit mannose-specific bacterial adhesion in a competitive manner. It has been found that mannosidic squaric acid monoamides serve especially well as inhibitors of type 1 fimbriae-mediated bacterial adhesion, but it has remained unclear whether this effect is due to specific inhibition of the bacterial lectin FimH or to unspecific bioconjugation between the lectin's carbohydrate binding site and a squaric acid monoamide. A bioconjugation reaction would result in a covalently crosslinked squaric acid diamide. Here it is shown that covalent inhibition of FimH by mannosidic squaric acid derivatives is very unlikely and that compounds of this type serve rather as excellent specific candidates for low-molecular-weight inhibitors of bacterial adhesion. This has been verified by testing the properties of glycosidic squaric acid monoamides in diamide formation, by two different adhesion assays with a series of selected control compounds, and by molecular docking studies that further support the results obtained in the bioassays. Candidates for specific antiadhesives: Squaric acid (SA) monoamides have the ability to crosslink unspecifically to amines. It has been shown that mannosidic SA monoamides serve as specific inhibitors of the bacterial lectin FimH and that no covalent bioconjugation within the lectin's carbohydrate binding site (CRD) occurs.

A kit for the investigation of live Escherichia coli cell adhesion to glycosylated surfaces

A combination of microtiter plate functionalization techniques and two facile bacterial adhesion inhibition assays form a flexible toolbox for the investigation of bacterial adhesion mechanisms on glycosylated surfaces.

Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays

Polyanionic glycopolymers were synthesized aiming at establishing a simple process for assembling glycosyl arrays. The synthetic glycopolymers carry the key carbohydrate epitopes of α-d-galactobioside (Gb2), β-lactoside, and α-d-mannopyranoside