10357-27-4

Basic information

• Product Name: 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE
• Synonyms: PNP-ALPHA-D-MAN;PNP ALPHA-D-MANNOPYRANOSIDE;PNP-ALPHA-D-MANNOSIDE;P-NITROPHENYL ALPHA-D-MANNOPYRANOSIDE;P-NITROPHENYL-ALPHA-D-MANNOSIDE;NITROPHENYL-A-D-MANNOPYRANOSIDE, 4-;MAN1-A-PNP;4-NITROPHENYL-A-D-MANNOSIDE
• CAS NO: 10357-27-4
• Molecular Formula: C₁₂H₁₅NO₈
• Molecular Weight: 301.25
• EINECS: 233-776-6
• Product Categories: Substrates;13C & 2H Sugars;Biochemistry;Glycosides;Sugars;Carbohydrates & Derivatives;ChromogenicEnzyme Substrates;Mannosidase, alpha-;Mannoside;Substrates by Enzyme;substrate
• Mol File: 10357-27-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 179-181 °C
• Boiling Point: 582.2 °C at 760 mmHg
• Flash Point: 305.9 °C
• Appearance: White to Off-white/Powder
• Density: 1.599 g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMF: 50 mg/mL, clear, very faintly yellow
• PKA: 12.55±0.70(Predicted)
• Water Solubility: Soluble in water at 10mg/ml
• BRN: 92210
• CAS DataBase Reference: 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE(10357-27-4)
• EPA Substance Registry System: 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE(10357-27-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 10357-27-4(Hazardous Substances Data)

Usage

Description

4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE, also known as p-Nitrophenyl α-D-Mannopyranoside (CAS# 10357-27-4), is a crystalline compound that plays a significant role in organic synthesis. It is a derivative of mannopyranoside, which is a type of sugar molecule commonly found in various biological systems. The nitrophenyl group attached to the sugar molecule provides unique chemical properties that make it valuable for various applications.

Uses

Used in Organic Synthesis:
4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE is used as a synthetic building block for the creation of complex organic molecules. Its unique structure allows for specific interactions with other molecules, making it a versatile component in the synthesis of various compounds.
Used in Glycosylation Reactions:
In the field of carbohydrate chemistry, 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE is used as a glycosyl donor in glycosylation reactions. These reactions are crucial for the formation of glycosidic bonds, which are essential for the structure and function of many biological molecules, such as glycoproteins and glycolipids.
Used in Enzyme Assays:
4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE is also used as a substrate in enzyme assays, particularly for the detection and quantification of glycosidase enzymes. The release of the nitrophenyl group upon enzymatic cleavage of the glycosidic bond results in a colorimetric change, allowing for the assessment of enzyme activity.
Used in Drug Development:
In the pharmaceutical industry, 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE can be used as a starting material for the development of new drugs targeting glycosidase enzymes, which are implicated in various diseases, including cancer, infectious diseases, and lysosomal storage disorders.
Used in Material Science:
The unique properties of 4-NITROPHENYL-ALPHA-D-MANNOPYRANOSIDE can also be exploited in the development of novel materials with specific interactions and properties, such as self-assembling systems or materials with tailored biocompatibility.

Upstream product

• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 
• 1262015-20-2 p-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-gulopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 7296-15-3 alpha-D-mannopyranoside 
• 100-02-7 4-nitro-phenol 
• 530-26-7 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 619-73-8 4-nitrobenzyl chloride 
• 83-87-4 D-Mannose pentaacetate 
• 243120-94-7 4-nitrobenzyl tetra-O-pivaloyl-α-D-mannopyranoside 

Downstream Products

• 34213-86-0 p-aminophenyl-α-D-mannopyranoside 
• 59571-75-4 methyl 2-O-α-D-mannopyranosyl-α-D-mannopyranoside 
• 78962-39-7 methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 
• 88493-81-6 p-nitrophenyl 3,6-di-O-benzyl-α-D-mannopyranoside 
• 80264-82-0 p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 334700-80-0 (2R,3S,4S,5S,6R)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-6-(4-nitro-phenoxy)-tetrahydro-pyran-3,4,5-triol 
• 16790-33-3 p-nitrophenyl 2-O-α-D-mannopyranosyl-α-D-mannopyranoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 211985-64-7 Toluene-4-sulfonic acid (2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester 
• 58056-41-0 p-nitrophenyl 4,6-O-benzylidene-α-D-mannopyranoside 
• 3458-28-4 D-Mannose 
• 1262015-21-3 p-nitrophenyl 4,6-O-benzylidene-β-D-gulopyranoside 
• 1283768-40-0 p-nitrophenyl β-D-fucopyranosyl-(1,3)-α-D-mannopyranoside 
• 101455-27-0 p-nitrophenyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 

Relevant articles and documents

Sulfatase-catalyzed assembly of regioselectively O-sulfonated p-nitrophenyl α-D-gluco- and α-D-mannopyranosides

A chemoenzymic methodology is extended to the library synthesis of regioselectively O-sulfonated pNP D-gluco and D-mannopyranosides. The method involves the sequential reactions of chemical O-sulfonation and sulfatase-catalyzed O-desulfonation. pNP 2,6-di-O-sulfo-α-D- glucopyranoside and pNP 3,6-di-O-sulfo-α-D-mannopyranoside were obtained as sodium salts using chemical methods by way of dibutylstannylene acetals or tributylstannyl ethers. They were then applied to enzyme reactions using three molluscan enzymes (snail, limpet, and abalone). The sulfatase reactions cleaved a sulfate group at the secondary O-2 or O-3 position to yield the corresponding pNP 6-O-sulfo sugars. Neither pNP 6-O-sulfo-α-D-glucopyranoside nor 6-O-sulfo-α-D-mannopyranoside became the enzyme substrate. Evidently, the molluscan sulfatases have a tendency to cleave the secondary O-sulfo group with assistance from the 6-O-sulfo group.

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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)

A process for preparing nitro phenyl - α - D - pyran honeydews glycoside method

The invention discloses a p-nitrophenyl-alpha-D-mannopyranoside preparation method. The p-nitrophenyl-alpha-D-mannopyranoside preparation method is characterized by including (1), in the presence of catalysts, enabling alpha-D-mannose under protection to contact with p-nitrophenol under the coupling reaction condition so as to obtain p-nitrophenyl-alpha-D-mannoside under protection; (2), subjecting the p-nitrophenyl-alpha-D-mannoside under protection, obtained in the step (1), to deprotection so as to obtain p-nitrophenyl-alpha-D-mannopyranoside. The p-nitrophenyl-alpha-D-mannopyranoside preparation method has the advantages of short reaction route, simplicity and convenience in operation, high yield, short reaction time and low cost.