Magenta‑Glc

Magenta‑Glc (CAS 93863‑89‑9), systematically 5‑bromo‑6‑chloro‑3‑indolyl β‑D‑glucopyranoside, is a synthetic β‑D‑glucosidase‑specific chromogenic substrate in which a 5‑bromo‑6‑chloro‑3‑indoxyl aglycone is linked via a β‑glycosidic bond to D‑glucose. When hydrolyzed by β‑D‑glucosidase or glucosidase‑containing enzymes, the indoxyl moiety is released and undergoes aerial oxidation to form an insoluble magenta‑colored indigo‑type pigment, enabling visual detection of enzyme activity. This substrate is widely used in selective culture media (e.g., for differentiation of Vibrio and other bacteria) and in enzyme‑kinetic assays for recombinant or purified β‑D‑glucosidases. Compared with standard X‑Glc‑type substrates, Magenta‑Glc produces a distinct reddish‑magenta color that improves contrast and readout in mixed microbial populations, making it particularly useful for taxonomic and phenotypic screening in microbiology.

Appearance

• Off‑white to pale yellow crystalline powder or lyophilized solid.
• Fine, free‑flowing texture suitable for accurate weighing and dissolution in aqueous or mixed solvents.

Source / synthesis

• Synthetically produced by coupling 5‑bromo‑6‑chloro‑3‑indoxyl with β‑D‑glucose under glycosylation conditions to form the β‑D‑glucopyranoside.
• Commercially manufactured by specialty carbohydrate and enzyme‑substrate suppliers as a high‑purity, research‑use‑only reagent.

Molecular weight and structure

• Molecular formula: C14H15BrClNO6C14​H15​BrClNO6​.
• Molecular weight: 408.60–408.63 g/mol.
• Structure: 5‑bromo‑6‑chloro‑1H‑indol‑3‑yl β‑D‑glucopyranoside, with a β‑glycosidic linkage between the indole C3‑O and the D‑glucose ring.

Sugar specificity

• Specifically hydrolyzed by β‑D‑glucosidases (EC 3.2.1.21) and closely related β‑D‑glucoside‑cleaving enzymes.
• Shows minimal cross‑reactivity with other β‑glycosidases (e.g., β‑galactosidase, β‑glucuronidase) under optimized assay conditions.

Biological activity

• Acts as a chromogenic reporter for β‑D‑glucosidase‑mediated hydrolysis of β‑D‑glucosyl linkages in glycosides and oligosaccharides.
• Enzymatic cleavage yields 5‑bromo‑6‑chloro‑3‑indoxyl, which oxidizes and dimerizes into a magenta‑colored, water‑insoluble dye, providing a sensitive, low‑background signal for solution‑based, gel‑based, and solid‑medium assays.

Purity and microbial contamination

• Typically supplied at ≥98% purity as determined by HPLC or equivalent analytical methods.
• Certificates of analysis generally confirm low levels of residual solvents, heavy metals, and absence of significant microbial contamination when stored and handled under aseptic conditions.

Identity and quality control

• Identity verified by NMR, HPLC, MS, and elemental analysis, with batch‑specific certificates of analysis provided by major suppliers.
• Quality‑control procedures include checks for appearance, solubility, UV/Vis spectral characteristics, and performance in a defined β‑D‑glucosidase activity assay.

Shelf life and storage

• Shelf life is typically 12–24 months when stored as a dry powder at –20 °C in a tightly sealed container, protected from moisture and light.
• Aqueous working solutions should be prepared immediately before use or stored frozen for short periods to minimize degradation and nonspecific oxidation of the indoxyl moiety.

Application

• Screening and differentiation of β‑D‑glucosidase‑producing microorganisms (e.g., Vibrio species and other bacteria) on selective agar media.
• Enzyme‑activity assays for recombinant or purified β‑D‑glucosidases in solution or immobilized formats.
• Phenotypic bacterial‑strain identification and taxonomic studies in microbiology.

Key characteristics

• High sensitivity and low background due to formation of an insoluble magenta‑colored dye upon β‑D‑glucosidase hydrolysis.
• Defined β‑D‑glucopyranoside linkage providing selectivity for β‑D‑glucosidases over other glycosidases.
• Crystalline, stable powder with a well‑defined molecular weight and formula suitable for quantitative enzyme assays and standardized media formulations.

citations 

• ChemicalBook – 5‑Bromo‑6‑chloro‑3‑indolyl‑β‑D‑glucopyranoside (Magenta‑Glc): https://www.chemicalbook.com/ChemicalProductProperty_US_CB9337260.aspx
• ChemicalBook – 5‑Bromo‑6‑chloro‑3‑indoxyl‑β‑D‑glucopyranoside product page (CAS 93863‑89‑9): https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9337260.htm
• ChemScene – 5‑Bromo‑6‑chloro‑3‑indolyl‑β‑D‑glucopyranoside: https://www.chemscene.com/93863-89-9.html
• Glycosynth – 5‑Bromo‑6‑chloro‑3‑indolyl β‑D‑glucopyranoside product page: https://www.glycosynth.co.uk/det/33/5-Bromo-6-chloro-3-indolyl-beta-D-glucopyranoside/
• Glycosynth – Certificate of Analysis for 5‑bromo‑6‑chloro‑3‑indolyl‑β‑D‑glucopyranoside (batch‑specific QC data): https://www.glycosynth.co.uk/userdata/files/cofa/31059-Wsample-COFA.pdf
• Pharmaffiliates – 5‑Bromo‑6‑chloro‑3‑indoxyl‑β‑D‑glucopyranoside catalog entry: https://www.pharmaffiliates.com/en/93863-89-9-5-bromo-6-chloro-3-indoxyl-beta-d-glucopyranoside-pa270029266.html
• ChemDad – 5‑Bromo‑6‑chloro‑3‑indoxyl‑β‑D‑glucopyranoside chemical‑data page: https://chemdad.com/index.php?c=article&id=49496
• Hepattack – Magenta‑Glc entry in catalog (CAS 93863‑89‑9): https://www.hepattack.com/en/product02_cid_213.html
• India‑Mart listing (Magenta‑β‑D‑glucoside, CAS 93863‑89‑9, distributor overview): https://www.indiamart.com/kemystery-chemicals-private-limited/industrial-chemicals.html
• Related β‑glucosidase‑substrate overview (for assay and application context): https://www.glycosynth.co.uk/ (enzyme‑substrate catalog section)