878495-64-8

Basic information

• Product Name: 5-BROMO-6-CHLORO-3-INDOLYL ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: 5-BROMO-6-CHLORO-3-INDOLYL ALPHA-D-GLUCOPYRANOSIDE;Magenta-alpha-glucoside;Magenta-α-D-Glc
• CAS NO: 878495-64-8
• Molecular Formula: C14H15BrClNO6
• Molecular Weight: 408.63
• Product Categories: substrate
• Mol File: 878495-64-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-BROMO-6-CHLORO-3-INDOLYL ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-6-CHLORO-3-INDOLYL ALPHA-D-GLUCOPYRANOSIDE(878495-64-8)
• EPA Substance Registry System: 5-BROMO-6-CHLORO-3-INDOLYL ALPHA-D-GLUCOPYRANOSIDE(878495-64-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 878495-64-8(Hazardous Substances Data)

Usage

Uses

Used in Microbiological Research:
5-Bromo-6-Chloro-3-Indolyl alpha-D-Glucopyranoside is used as a detection agent for β-D-glucosidase activity in microbiological research. It allows for the identification of this enzyme, which is crucial for understanding the metabolic pathways and enzymatic functions in microorganisms.
Used in Assay Development:
In assay development, 5-Bromo-6-Chloro-3-Indolyl alpha-D-Glucopyranoside is used as a key component for creating tests that measure β-D-glucosidase activity. Its interaction with the enzyme results in a blue precipitate, offering a simple and sensitive method for quantifying the enzyme's activity in different biological samples.
Used in Enzyme Activity Studies:
5-Bromo-6-Chloro-3-Indolyl alpha-D-Glucopyranoside is utilized as a research tool for studying the activity of β-D-glucosidase in various biological systems. Its specific interaction with the enzyme aids in understanding the enzyme's role in biological processes and its potential applications in medicine and biotechnology.

Upstream product

• 910123-20-5 5-bromo-4-chloroisatoic anhydride 
• 1607828-46-5 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]isatoic anhydride 
• 1607828-49-8 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester 
• 1607828-51-2 5-bromo-6-chloroindoxylic acid allyl ester 
• 1607828-57-8 C₂₆H₂₇BrClNO₁₂ 
• 96414-42-5 (N-acetyl-5-bromo-6-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 50419-88-0 2-amino-5-bromo-4-chlorobenzene carboxylic acid 
• 1607828-44-3 N-acetyl-5-bromo-4-chloroanthranilic acid 
• 5900-55-0 N-(5-chloro-2-methylphenyl)acetamide 
• 1607828-43-2 N-(4-bromo-5-chloro-2-methylphenyl)-acetamide 

Relevant articles and documents

Synthesis of precipitating chromogenic/fluorogenic β-glucosidase/β-galactosidase substrates by a new method and their application in the visual detection of foodborne pathogenic bacteria

We developed a new efficient method for the synthesis of important indoxyl glycoside substrates for β-glucosidase and β-galactosidase by using 1-acetylindol-3-ones as intermediates. This method was used to synthesise novel precipitating fluorogenic substrates for β-glucosidase based on 2-(benzothiazol-2′-yl)-phenols. We also assessed the application of these substrates in the detection of foodborne pathogenic bacteria.

Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative

The invention discloses a synthesis method of glucoside based on an indoxyl derivative and a 2-(benzothiazol-2'-yl)phenol derivative. The general formula of a synthetic equation of the synthesis method is as shown in the description; the Ar-OH represents aromatic phenol or a ketonic compound thereof, and is used as a glycosyl receptor in a glycosylation reaction; the G-X represents halogenated sugar, and is used as a glycosyl donor in the glycosylation reaction. According to the synthesis method of the glucoside based on the indoxyl derivative and the 2-(benzothiazol-2'-yl)phenol derivative, a 1-acetylindolin-3-one derivative is selected and used as an intermediate; a novel synthesis method is researched and developed to prepare the glucoside based on the indoxyl derivative; a novel glycosidase fluorescence probe based on a BTP ((2-benzothiazol-2'-yl)phenyl) derivative is synthesized by applying the method; meanwhile, the application effects of the glucoside based on the indoxyl derivative and the glycosidase fluorescence probe are investigated. The glucoside based on the indoxyl derivative and the 2-(benzothiazol-2'-yl)phenol derivative can be used as glycosidase substrates, and is used for the positioning analytic detection and screening on the corresponding glycosidase, a microorganism using the corresponding glycosidase as a characteristic target, and the like.

Indoxylic acid esters as convenient intermediates towards indoxyl glycosides

Indoxylic acid methyl and allyl esters with varied halide-substitution patterns were obtained in excellent yields using a scalable route. Phase-transfer glycosylation of these key intermediates was carried out with various glycosyl halides. Subsequent mild silver-mediated decarboxylation followed by Zemplen deacetylation led to indoxyl glycosides in good overall yields. Indoxyl glycosides are well-established and widely used tools for enzyme screening and enzyme-activity monitoring. In the past, their synthesis has been difficult, so this new approach has led to a variety of useful structures. Indoxyl glycosides with varied halide-substitution patterns were synthesized using indoxylic acid esters as key intermediates. Glycosylation under phase-transfer conditions, ester cleavage, and mild decarboxylation led to the indoxyl glycosides in good yields. This approach enables access to a number of different indoxyl compounds. Copyright