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N,N',N''-Triacetylchitotriose

Catalog No.
C3802
Chitinase substrate, used for glycobiology and pathogen interaction mechanism research.
Grouped product items
SizePriceStock Qty
1mg
$83.00
In stock
5mg
$122.00
In stock
10mg
$171.00
In stock
50mg
$521.00
In stock
100mg
$885.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

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Background

N,N',N''-Triacetylchitotriose (CAS No.: 38864-21-0) is a well-defined chitin-derived oligosaccharide composed of three N-acetylglucosamine residues and is widely utilized as a biologically active probe in glycobiology and host–pathogen interaction studies. As a representative chitooligosaccharide, it serves as a substrate for chitinases and chitosanases, enabling detailed investigation of enzymatic degradation mechanisms in microbial systems, while also functioning as a ligand for specific carbohydrate-recognition proteins and receptors that modulate signaling pathways involved in immune and plant defense responses. It has been characterized as a competitive inhibitor of lysozyme, attenuating its enzymatic activity and reducing membrane fusion events in lysozyme-associated model systems, thereby providing insight into lysozyme-mediated processes. Additionally, this compound exhibits antioxidant properties, including the ability to scavenge reactive oxygen species and protect nucleic acids from oxidative damage, supporting its utility in studies of oxidative stress. In vitro, its modulatory effects on enzyme activity and binding interactions are typically observed in the low micromolar to millimolar concentration range, depending on assay conditions. N,N',N''-Triacetylchitotriose is broadly applied in biochemical assays, receptor binding studies, and cell-based models to elucidate oligosaccharide-mediated signaling and enzyme specificity, with experimental concentrations tailored to specific research objectives in drug discovery and mechanistic biology.

Chemical Properties

Physical AppearanceA solid
Storage-20°C
M.Wt627.59
Cas No.38864-21-0
FormulaC24H41N3O16
SynonymsTri-N-acetyl-Chitotriose; Tri-N-acetyl-D-Glucosamine
Solubilityinsoluble in DMSO; insoluble in EtOH; ≥8.07 mg/mL in H2O
Chemical NameN-((2S,3R,4R,5S,6R)-2-(((2R,3S,4R,5R)-5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy)-5-(((2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
Canonical SMILESO=C(C)N[C@@H]([C@@](O[C@@]([C@H](O)CO)([H])[C@H](O)[C@H](C=O)NC(C)=O)([H])O[C@@H]1CO)[C@@H](O)[C@@H]1O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

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