X-NeuNAc CHX Salt

X-NeuNAc CHX Salt (5-Bromo-4-chloro-3-indolyl-α-N-acetylneuraminic acid ,cyclohexylammonium salt) is a chromogenic substrate specifically developed for histochemical and biochemical detection of sialidase (neuraminidase, EC 3.2.1.18) activity in microbial pathogenesis, viral infection studies, and glycobiology research. Hydrolysis by sialidases cleaves the α-2,3/α-2,6-glycosidic linkage, releasing 5-bromo-4-chloro-3-indoxyl, which rapidly oxidizes and dimerizes to form an insoluble dark blue pigment, enabling precise spatial localization of enzyme activity without product diffusion. The cyclohexylammonium (CHX) salt enhances water solubility (>5 mg/mL) over sodium forms, making it ideal for tissue section staining, bacterial colony screening (Vibrio cholerae, Clostridium perfringens), live-cell imaging of sialidase activity, and high-throughput screening of viral neuraminidase inhibitors, offering superior sensitivity and permanence compared to fluorescent MU-NeuNAc substrates.

Appearance

White to pale beige crystalline powder, odorless and hygroscopic.
Freely soluble in water/DMF (5-15 mM); forms stable colorless solutions.

Source

Glycosylation of 5-bromo-4-chloro-3-indolol with peracetylated α-NeuNAc donor (Fischer-Ziegler), followed by deprotection and CHX salt formation.
Specialized synthesis for glycobiology research; research grade ≥98%.

Molecular Weight and Structure

C25H35BrClN3O9, 636.92 g/mol (salt); free acid C19H21BrClN2O9 = 523.74 g/mol.
α-Neu5Ac-(2→3)-5-Br-4-Cl-indolyl; cyclohexylammonium counterion.

Sugar Specificity

Specific for α-2,3/α-2,6-sialidases (bacterial/viral); Km 0.1-0.5 mM.
Hydrolyzed by Clostridium/Vibrio neuraminidases; minimal mammalian activity.

Biological Activity

Sialidase cleavage → indolyl + Neu5Ac → dark blue insoluble pigment.
Optimal pH 6.0-7.5, 37°C; visible staining 30 min-2h; stable product.

Purity and Microbial Contamination

≥98% HPLC purity; α-anomer >97%; free indoxyl <0.1%.
Endotoxin-free; sterile lyophilized; no contaminating sialidase.

Identity and Quality Control

LC-MS (m/z 524.1 [M-H]-), 1H-NMR (α-NeuNAc H-3ax/eq), functional staining assay.
TLC single spot; CAS-equivalent verification for research standards.

Shelf Life and Storage

24-36 months desiccated -20°C; amber vials, argon atmosphere.
Aqueous stocks stable 3 months -20°C; avoid light/freeze-thaw.

Application

Bacterial sialidase detection (V. cholerae, C. perfringens) on agar plates.
Viral neuraminidase inhibitor screening (influenza, parainfluenza).
Histochemical localization in tissue sections, live-cell imaging.

Key Characteristics

Insoluble blue pigment prevents diffusion; permanent staining.
CHX salt superior solubility vs. sodium salt; non-toxic; high contrast.

Citation Links

Name	X-NeuNAc CHX Salt
synonyms	5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid, cyclohexylammonium salt
CAS Number	N/A
Molecular Formula	C25H35BrClN3O9
Molecular Weight	636.92
Specifications & Purity	98%
Package	Vacuum foil packaging

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Name	Resorufin-Glc Sodium Salt
Synonyms	Resorufin-β-D-glucuronide sodium salt
CAS Number	12540-91-7
Molecular Formula	C18H14NNaO9
Molecular Weight	431.30 g/mol
Specifications & Purity	≥95% (Vacuum foil packaging)

Name	X-β-L-Fuc
Synonyms	5-Bromo-4-chloro-3-indolyl-β-L-fucopyranoside
CAS Number	125280-49
Molecular Formula	C14H15BrClNO5
Molecular Weight	392.63 g/mol
Specifications & Purity	≥95% (Vacuum foil packaging)

Name	8HQ-Gal
Synonyms	8-Hydroxyquinolyl-β-D-galactopyranoside
CAS Number	110379-84-8
Molecular Formula	C15H17NO6
Molecular Weight	307.30 g/mol
Specifications & Purity	98% (Vacuum foil packaging)

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X-NeuNAc CHX Salt

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