41341-55-3

Basic information

• Product Name: 4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside
• Synonyms: 4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside;4'-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranosid;4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-thiogalactopyranoside
• CAS NO: 41341-55-3
• Molecular Formula: C₂₀H₂₃NO₁₁S
• Molecular Weight: 485.4617
• Product Categories: Carbohydrates
• Mol File: 41341-55-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 575.4°Cat760mmHg
• Flash Point: 301.8°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 3.04E-13mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside(41341-55-3)
• EPA Substance Registry System: 4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside(41341-55-3)

Safety Data

• Hazardous Substances Data: 41341-55-3(Hazardous Substances Data)

Usage

Description

4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside is a chemical compound that serves as a chromogenic substrate in biochemical research, specifically for the detection of beta-galactosidase activity. This synthetic substrate is sensitive to enzymatic hydrolysis, resulting in a color change from colorless to yellow when cleaved by the enzyme. It is widely used in assays to measure the activity of beta-galactosidase, an enzyme crucial in the metabolism of lactose and other carbohydrates. Furthermore, it is utilized as a tool in molecular biology to study gene expression and regulation.

Uses

Used in Biochemical Research:
4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside is used as a chromogenic substrate for detecting beta-galactosidase activity, allowing researchers to monitor enzymatic activity through a visible color change.
Used in Enzyme Activity Assays:
4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside is employed as a substrate in assays designed to measure the activity of beta-galactosidase, providing a quantitative assessment of the enzyme's function in the metabolism of lactose and other carbohydrates.
Used in Molecular Biology:
4-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside is used as a tool in molecular biology to study gene expression and regulation, offering insights into the mechanisms underlying various biological processes.

InChI:InChI=1/C20H23NO11S/c1-10(22)28-9-16-17(29-11(2)23)18(30-12(3)24)19(31-13(4)25)20(32-16)33-15-7-5-14(6-8-15)21(26)27/h5-8,16-20H,9H2,1-4H3

Upstream product

• 1849-36-1 para-nitrobenzenethiol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 84062-53-3 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 
• 4163-60-4 β-D-galactose peracetate 
• 40591-65-9 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 
• 350-46-9 4-Fluoronitrobenzene 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 

Downstream Products

• 1230-27-9 p-nitrophenyl 1-thio-β-D-galactopyranoside 
• 167084-08-4 4-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside 
• 167084-07-3 4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of Pseudomonas aeruginosa

Chronic infections by Pseudomonas aeruginosa are characterized by biofilm formation, which effectively enhances resistance toward antibiotics. Biofilm-specific antibiotic delivery could locally increase drug concentration to break antimicrobial resistance and reduce the drug's peripheral side effects. Two extracellular P. aeruginosa lectins, LecA and LecB, are essential structural components for biofilm formation and thus render a possible anchor for biofilm-targeted drug delivery. The standard-of-care drug ciprofloxacin suffers from severe systemic side effects and was therefore chosen for this approach. We synthesized several ciprofloxacin-carbohydrate conjugates and established a structure-activity relationship. Conjugation of ciprofloxacin to lectin probes enabled biofilm accumulation in vitro, reduced the antibiotic's cytotoxicity, but also reduced its antibiotic activity against planktonic cells due to a reduced cell permeability and on target activity. This work defines the starting point for new biofilm/lectin-targeted drugs to modulate antibiotic properties and ultimately break antimicrobial resistance.

Application of halide molten salts as novel reaction media for O-glycosidic bond formation

In this study we have explored the application of halide molten salts as reaction media for O-glycosidic bond formation under basic conditions and mild heating. Eighteen different room-temperature ionic liquids and molten salts, representing four different classes of cations (i.e. imidazolium, pyridinium, pyrrolidinium and ammonium), were screened in the glycosidation reaction of p-nitrophenol with aceto-bromo-α-D-galactose. 1-Butyl-4-methylimidazolium chloride (BMIM·Cl) gave the best results and was applied in the reactions of other phenolic substrates to give the products with up to 80% yields. All the reactions were highly selective to give the β-anomers, and the molten salt BMIM·Cl could easily be reused with no apparent loss in activity.

Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-β-d-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for