5-Bromo-6-chloro-1H-indol-3-yl alpha-D-galactopyranoside
[CAS# 198402-60-7]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: 5-Bromo-6-chloro-1H-indol-3-yl alpha-D-galactopyranoside
• Synonyms: (2R,3R,4S,5R,6R)-2-[(5-bromo-6-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Molecular Formula: C₁₄H₁₅BrClNO₆
• Molecular Weight: 408.63
• CAS Registry Number: 198402-60-7
• SMILES: C1=C2C(=CC(=C1Br)Cl)NC=C2O[C@@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O

Properties

• Density: 1.9±0.1 g/cm³ Calc.^*
• Boiling point: 673.9±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 361.3±31.5 °C (Calc.)^*
• Index of refraction: 1.732 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+312+332-H319-H335
• Safety Statements: P280

Discovery and Applications

5-Bromo-6-chloro-1H-indol-3-yl alpha-D-galactopyranoside is a synthetic derivative of indole, characterized by the presence of bromine and chlorine atoms substituted at the 5 and 6 positions of the indole ring, respectively. The molecule is glycosylated with an alpha-D-galactopyranoside moiety attached at the 3-position of the indole structure. This glycosidic linkage imparts distinct biochemical properties and improves the compound’s solubility and interaction with biological targets.

The synthesis of 5-bromo-6-chloro-1H-indol-3-yl alpha-D-galactopyranoside generally involves selective halogenation of the indole core followed by enzymatic or chemical glycosylation. Such compounds are often produced in the context of biochemical research aiming to study carbohydrate-protein interactions or to develop novel biochemical probes.

In application, halogenated indole glycosides like this compound are used as substrates or inhibitors in enzymatic assays, particularly those involving glycosidases or glycosyltransferases. Their modified indole scaffold allows for spectroscopic detection due to characteristic absorbance or fluorescence properties, facilitating enzyme activity monitoring.

Moreover, derivatives of halogenated indole glycosides have been investigated for their antimicrobial, antifungal, and anticancer activities. The introduction of halogen atoms is known to affect lipophilicity and membrane permeability, potentially enhancing biological activity.

In research, this compound contributes to the understanding of the role of glycosylation in biological recognition processes and enzyme specificity. Its structural features make it a valuable tool for designing inhibitors or substrates in glycobiology.

Although detailed pharmacological and toxicological profiles are less established for this specific compound compared to classical indole derivatives, the general class of halogenated indole glycosides is recognized for diverse bioactivities, prompting ongoing investigations.

Overall, 5-bromo-6-chloro-1H-indol-3-yl alpha-D-galactopyranoside represents a specialized chemical entity with applications primarily in biochemical research focused on enzyme interactions and the development of molecular probes.

References

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