Magenta‑α‑L‑Fucoside

Magenta‑α‑L‑Fucoside (CAS 1222705‑28‑3) is a synthetic α‑L‑fucosidase‑specific chromogenic substrate in which a 5‑bromo‑6‑chloro‑3‑indolyl aglycone is linked via an α‑glycosidic bond to α‑L‑fucopyranose. When hydrolyzed by α‑L‑fucosidases, the glycosidic bond is cleaved to release the indole derivative and α‑L‑fucose; the indole then undergoes air oxidation to form a strongly colored magenta‑ or blue‑colored precipitate or dye at the enzyme‑activity site. This reaction makes Magenta‑α‑L‑Fucoside especially useful for histochemical staining of α‑L‑fucosidase activity in cells, tissues, and microbial colonies, as well as for high‑throughput screening of enzyme‑expressing clones or recombinant α‑fucosidases. The compound is typically supplied as a high‑purity, lyophilized or crystalline solid, and is compatible with standard aqueous or buffer‑based incubation systems. Magenta‑α‑L‑Fucoside is widely used in glycobiology, microbiology, and cell biology to visualize α‑L‑fucosidase‑dependent cleavage of fucosylated glycoconjugates, including studies of lysosomal and bacterial α‑fucosidases classified in glycoside hydrolase families GH‑29 and GH‑95.

Appearance

Off‑white to pale yellow crystalline or lyophilized powder.
Forms a pale yellow to colorless solution in aqueous buffer; develops a magenta‑ or blue‑colored precipitate only after enzymatic hydrolysis and oxidation of the indole‑type chromophore.

Source / synthesis

Synthetically prepared by glycosylation of 5‑bromo‑6‑chloro‑3‑indole with α‑L‑fucopyranose or a protected α‑L‑fucoside, followed by deprotection and crystallization from aqueous or mixed‑solvent systems.
Commercially supplied by Chinese‑based glycobiology and enzyme‑substrate manufacturers (e.g., Hepattack, GeneseqTools) as a research‑grade α‑L‑fucosidase substrate.

Molecular weight and structure

Molecular formula: $C_{14} H_{15} BrClNO_{5}$ .
Molecular weight: 392.63 g/mol.
Structure: 5‑bromo‑6‑chloro‑3‑indol‑α‑L‑fucopyranoside, with an α‑glycosidic linkage between the indole‑type aglycone and the anomeric carbon of α‑L‑fucopyranose.

Sugar specificity

Specifically hydrolyzed by α‑L‑fucosidases (e.g., GH‑29 and GH‑95‑type fucosidases) that cleave α‑L‑fucosyl linkages in glycoproteins, glycolipids, and other fucosylated structures.
Frequently used in chromogenic panels and histochemical assays to distinguish α‑L‑fucosidase activity from other glycosidases in microbial and mammalian systems.

Biological activity

Serves as a chromogenic reporter whose rate of indole‑derivative release under defined pH and temperature conditions reflects α‑L‑fucosidase activity.
Enables localization and relative quantification of α‑L‑fucosidase activity in tissue sections, cell cultures, and microbial colonies, supporting studies on lysosomal‑glycosidase function and microbial‑carbohydrate‑metabolism pathways.

Purity and microbial contamination

Typically supplied as a high‑purity, “high‑purity raw material” (e.g., described as high‑purity lyophilized powder), suitable for research‑use‑only enzymatic assays.
Described as a non‑sterile, research‑grade solid; used under standard clean‑laboratory or sterile‑handling conditions depending on the assay (e.g., histochemistry vs. colony‑screening).

Identity and quality control

Identity based on CAS 1222705‑28‑3, molecular formula $C_{14} H_{15} BrClNO_{5}$ , and molecular weight 392.63 g/mol, with 5‑bromo‑6‑chloro‑3‑indol‑α‑L‑fucopyranoside as the systematic name.
Quality‑control generally includes checks for appearance, solubility, spectral properties, and performance in a defined α‑L‑fucosidase assay (e.g., histochemical or colorimetric screening for α‑fucosidase expression).

Shelf life and storage

Shelf life is typically 12–24 months when stored at −20 °C in a tightly sealed, light‑protected container, as the indole‑type chromophore is sensitive to light and oxidation.
Aqueous working solutions are best prepared fresh or used immediately, as prolonged storage or exposure to air can cause premature color development or background staining.

Application

Histochemical and chromogenic staining of α‑L‑fucosidase activity in tissue sections, cell cultures, and microbial colonies.
Screening of α‑L‑fucosidase‑expressing clones in recombinant enzyme‑expression or mutagenesis studies.
Use in glycobiology and microbiology to visualize α‑L‑fucosidase‑dependent processing of fucosylated glycoconjugates and to study lysosomal and bacterial fucosidase function.

Key characteristics

Chromogenic readout: release of an indole derivative that oxidizes to a magenta‑ or blue‑colored precipitate, enabling easy visual detection of α‑L‑fucosidase activity.
Defined α‑L‑fucopyranoside linkage providing selectivity for α‑L‑fucosidases over many other glycosidases.
High‑purity, lyophilized solid with a known molecular formula and weight, suitable for histochemical, colony‑, and microplate‑based assays.

Citations

Hepattack – Magenta‑α‑L‑Fucoside product page (CAS 1222705‑28‑3, MF C₁₄H₁₅BrClNO₅, MW 392.63): https://www.hepattack.com/en/product03_cid_213_pid_1079.html
GeneseqTools (Chinese‑language news) – Magenta‑α‑L‑Fucoside description (CAS 1222705‑28‑3, also named 5‑bromo‑6‑chloro‑3‑indol‑α‑L‑fucopyranoside): http://www.geneseqtools.com/cn/news-detail_cid_26_id_29.html
Mini‑review on microbial α‑L‑fucosidases (context for α‑fucosidase function and substrate specificity): https://pmc.ncbi.nlm.nih.gov/articles/PMC10154630/
Structural paper on α‑fucosidase mechanism (relevant to α‑L‑fucosidase‑substrate interactions): https://www.nature.com/articles/s41467-020-20044-z
α‑L‑Fucosidase assay‑kit technical manual (describes use of synthetic α‑fucosidase substrates, including chromogenic types): https://www.assaygenie.com/content/BN%20Technical%20Manuals/BN00771.pdf
Activity‑based protein‑profiling study involving α‑L‑fucosidases (general context for α‑fucosidase assays): https://pmc.ncbi.nlm.nih.gov/articles/PMC6471298/
Fucose‑glycobiology overview (background on fucosylated structures and fucosidase substrates): https://www.ncbi.nlm.nih.gov/pmc/ (search “fucose glycosylated structures α‑fucosidase”).
General glycosidase‑substrate catalog (Magenta‑α‑L‑Fucoside and related indolyl‑fucoside reagents overview): https://www.chemicalbook.com/ (search for “1222705‑28‑3”).
L‑fucose supplier‑page (for context on fucosidase‑natural substrates): https://www.alphachemika.co/chemical/4196/L-–-FUCOSE.html
Wikipedia‑entry on fucose (background on fucosidase‑substrate structures): https://en.wikipedia.org/wiki/Fucose

Product Name	Magenta-α-L-Fucoside
Chemical Name	5-Bromo-6-chloro-3-indolyl α-L-fucopyranoside
CAS Number	1222705-28-3
Molecular Formula	C14H15BrClNO5
Molecular Weight	392.63
Purity	98%
Packaging	Vacuum foil packaging

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Name	CNP-α-L-Fuc
Synonyms	2-Chloro-4-nitrophenyl-α-L-fucopyranoside
CAS Number	157843-41-9
Molecular Formula	C12H14ClNO7
Molecular Weight	319.70 g/mol
Specifications & Purity	98% (Vacuum foil packaging)

Name	Purple-Gal
Synonyms	5-Iodo-3-indolyl-β-D-galactopyranoside
CAS Number	306473-36-6
Molecular Formula	C14H16INO6
Molecular Weight	421.18 g/mol
Specifications & Purity	≥95% (Vacuum foil packaging)

Name	X-Gal
Synonyms	5-Bromo-4-chloro-3-indolyl-β-D-galactopyranoside
CAS Number	7270-6
Molecular Formula	C14H15BrClNO6
Molecular Weight	408.63 g/mol
Specifications & Purity	≥95% (Vacuum foil packaging)

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