5-Bromo-4-chloro-3-indolyl-beta-D-glucoside
[CAS# 15548-60-4]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside
• Synonyms: 5-Bromo-4-chloro-3-indolyl-beta-D-glucopyranoside; X-Glc; X-glucoside
• Molecular Formula: C₁₄H₁₅BrClNO₆
• Molecular Weight: 408.63
• CAS Registry Number: 15548-60-4
• EC Number: 239-603-0
• SMILES: C1=CC(=C(C2=C1NC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl)Br

Properties

• Melting point: 249-251 °C
• alpha: -81 ° (c=1, DMF)
• Boiling point: 698.0±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 375.9±31.5 °C (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside is a synthetic compound commonly used as a chromogenic substrate in enzymatic assays, particularly for detecting beta-glucosidase activity. The molecule consists of an indole derivative substituted with bromine and chlorine atoms at the 5 and 4 positions, respectively, linked to a beta-D-glucose moiety via a glycosidic bond. This structure allows the compound to act as a substrate for beta-glucosidase enzymes, which cleave the glycosidic bond, releasing the indolyl aglycone.

The discovery of this compound arose from the need for sensitive and specific substrates in enzymology and molecular biology. The presence of the 5-bromo and 4-chloro substitutions on the indolyl ring enhances the chromogenic properties of the released aglycone, allowing for improved visualization and quantification in various assays. Upon enzymatic cleavage, the liberated indolyl derivative undergoes oxidation and dimerization, producing a colored precipitate that is easily detectable by spectrophotometric or visual methods.

Applications of 5-bromo-4-chloro-3-indolyl-beta-D-glucoside are widespread in biochemical research and diagnostic contexts. It is frequently employed in histochemical staining to localize beta-glucosidase activity in tissues or cells. The substrate is also used in high-throughput screening assays to identify inhibitors or activators of beta-glucosidase, which is relevant in studying diseases such as Gaucher's disease and other lysosomal storage disorders where beta-glucosidase function is impaired.

In microbiology, this compound serves as a useful tool for detecting beta-glucosidase-producing microorganisms. Its use in selective media enables the differentiation of microbial species based on enzymatic activity, aiding in identification and characterization.

Overall, 5-bromo-4-chloro-3-indolyl-beta-D-glucoside is a valuable chromogenic substrate that supports research and diagnostic applications centered on beta-glucosidase activity. Its chemical design facilitates sensitive and specific detection, contributing significantly to enzymology, microbiology, and pathology.

References

1988. Novel compound for identifying Escherichia coli. Applied and Environmental Microbiology, 54(7).
DOI: 10.1128/aem.54.7.1874-1875.1988

2010. Characterization of a heat resistant beta-glucosidase as a new reporter in cells and mice. BMC Biology, 8.
DOI: 10.1186/1741-7007-8-89

2014. A reporter mouse line with doxycyclin-inducible expression of β-glucosidase. Histochemistry and Cell Biology, 142(5).
DOI: 10.1007/s00418-014-1255-5