3150-24-1

Basic information

• Product Name: 4-Nitrophenyl-beta-D-galactopyranoside
• Synonyms: 4-NITROPHENYL-B-D-GALACTOSIDE;4-NITROPHENYL-BETA-D-GALACTOSIDE;4-NITROPHENYL BETA-D-GALACTOSIDE-(1,5);4-NITROPHENYL-BETA-D-GALAKTOPYRANOSIDE;NITROPHENYL-B-D-GALACTOPYRANOSIDE, 4-;P-NITROPHENYL BETA-D-GALACTOPYRANOSIDE;P-NITROPHENYL BETA-D-GALACTOSIDE;PNPG
• CAS NO: 3150-24-1
• Molecular Formula: C₁₂H₁₅NO₈
• Molecular Weight: 301.25
• EINECS: 221-584-5
• Product Categories: Substrates;Biochemistry;Galactose;Glycosides;Sugars;Carbohydrates & Derivatives;substrate
• Mol File: 3150-24-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 178-182 °C
• Boiling Point: 442.39°C (rough estimate)
• Flash Point: 305.9 °C
• Appearance: white to light yellow crystalline powder
• Density: 1.3709 (rough estimate)
• Vapor Pressure: 2.14E-14mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• PKA: 12.55±0.70(Predicted)
• Water Solubility: Soluble in DMSO, Methanol, Water.
• BRN: 92213
• CAS DataBase Reference: 4-Nitrophenyl-beta-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenyl-beta-D-galactopyranoside(3150-24-1)
• EPA Substance Registry System: 4-Nitrophenyl-beta-D-galactopyranoside(3150-24-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 3150-24-1(Hazardous Substances Data)

Usage

Description

4-Nitrophenyl-beta-D-galactopyranoside, with the CAS number 3150-24-1, is a chemical compound that features a beta-D-galactopyranoside with a 4-nitrophenyl substituent at the anomeric position. It is a white to light yellow crystalline powder and is primarily used in organic synthesis.

Uses

1. Used in Organic Synthesis:
4-Nitrophenyl-beta-D-galactopyranoside is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows for specific reactions and modifications, making it a valuable component in the synthesis of complex organic molecules.
2. Used in Enzyme Assays:
In the field of biochemistry and molecular biology, 4-Nitrophenyl-beta-D-galactopyranoside is used as a substrate in enzyme assays, particularly for the detection and quantification of beta-galactosidase activity. 4-Nitrophenyl-beta-D-galactopyranoside serves as a colorimetric indicator, allowing researchers to monitor enzyme activity through the release of the yellow 4-nitrophenol upon enzymatic cleavage.
3. Used in Analytical Chemistry:
4-Nitrophenyl-beta-D-galactopyranoside is also utilized in analytical chemistry for the development of new methods and techniques for the detection and quantification of specific enzymes or other biomolecules. Its distinct chemical properties make it a suitable candidate for the creation of novel analytical protocols.
4. Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-Nitrophenyl-beta-D-galactopyranoside may be employed as a starting material for the development of new drugs targeting enzymes involved in various diseases. Its unique structure can be modified to create potential drug candidates with specific biological activities.
5. Used in Material Science:
4-Nitrophenyl-beta-D-galactopyranoside's properties may also find applications in material science, particularly in the development of new materials with specific interactions or properties. Its ability to form complexes with other molecules could be exploited to create materials with tailored characteristics for various applications.

Purification Methods

Purify the galactoside by recrystallisation from EtOH. [Horikoshi J Biochem (Tokyo) 35 39 1042, Goebel & Avery J Exptl Medicine 50 521 1929, Snyder & Link J Am Chem Soc 7 5 1758.] It is a chromogenic substrate for -galactosidases [Buoncore et al. J Appl Biochem 2 390 1980]. [Beilstein 17/7 V 55.]

InChI:InChI=1/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8?,9-,10+,11?,12+/m0/s1

Upstream product

• 10357-27-4 4-nitrophenyl-α-D-mannopyranoside 
• 100-02-7 4-nitro-phenol 
• 4163-60-4 β-D-galactose peracetate 
• 1262015-20-2 p-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-gulopyranoside 
• 10257-28-0 D-Galactose 
• 108-24-7 acetic anhydride 
• 81119-31-5 4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside 
• 17042-39-6 p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 2872-66-4 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 5094-33-7 p-aminophenyl β-D-galactopyranoside 
• 161976-09-6 phenyl (2,3,4,6-tetra-O-acetyl-β-D-galacto-pyranosyl)-(1->6)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 59-23-4 D-Galactose 
• 71630-16-5 3-O-β-D-Galactopyranosyl-β-D-galactopyranose 
• 124580-30-9 methyl β-D-galactopyranosyl-(1,3)-α-D-galactopyranoside 
• 111002-20-1 Methyl 6-O-β-D-galactopyranosyl-α-D-galactopyranoside 
• 100836-88-2 Galβ(1-3)GlcNAcβ(1-)OCH3 
• 68774-40-3 N-acetyllactosamine methyl glycoside 
• 114102-85-1 p-nitrophenyl β-D-galactopyranoside 6-(diphenylphosphate) 
• 161976-15-4 Acetic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-phenylsulfanyl-6-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 
• 102717-05-5 p-nitrophenyl 6-O-trityl-β-D-galactopyranoside 
• 81123-28-6 4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranoside 
• 64970-92-9 4-nitrophenyl 3,4-O-isopropylidene-β-D-galactopyranoside 
• 64970-96-3 p-nitrophenyl 4,6-O-isopropylidene-β-D-galactopyranoside 

Relevant articles and documents

Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water

Reducing sugars may be directly converted into the corresponding para-nitrophenyl (pNP) glycosides using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), para-nitrophenol, and a suitable base in aqueous solution. The reaction is stereoselective for sugars with either a hydroxyl or an acetamido group at position 2, yielding the 1,2-trans pNP glycosides. A judicious choice of base allows extension to di-and oligosaccharide substrates, including a complex N-glycan oligosaccharide isolated from natural sources, without the requirement of any protecting group manipulations

Development and optimization of a competitive binding assay for the galactophilic low affinity lectin LecA from: Pseudomonas aeruginosa

Infections with the Gram-negative bacterium Pseudomonas aeruginosa result in a high mortality among immunocompromised patients and those with cystic fibrosis. The pathogen can switch from planktonic life to biofilms, and thereby shields itself against antibiotic treatment and host immune defense to establish chronic infections. The bacterial protein LecA, a C-type lectin, is a virulence factor and an integral component for biofilm formation. Inhibition of LecA with its carbohydrate ligands results in reduced biofilm mass, a potential Achilles heel for treatment. Here, we report the development and optimization of a fluorescence polarization-based competitive binding assay with LecA for application in screening of potential inhibitors. As a consequence of the low affinity of d-galactose for LecA, the fluorescent ligand was optimized to reduce protein consumption in the assay. The assay was validated using a set of known inhibitors of LecA and IC50 values in good agreement with the known Kd values were obtained. Finally, we employed the optimized assay to screen sets of synthetic thio-galactosides and natural blood group antigens and report their structure-activity relationship. In addition, we evaluated a multivalent fluorescent assay probe for LecA and report its applicability in an inhibition assay.

Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library

A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.