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N,N′,N′′-Triacetylchitotriose

SIGMA/T2144 - ≥93% (HPLC)

Synonym: NAG3; Tri(N-acetyl-D-glucosamine); O-[2-Acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-O-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-2-acetamido-2-deoxy-D-glucopyranose

CAS Number: 38864-21-0
Empirical Formula (Hill Notation): C24H41N3O16
Molecular Weight: 627.59
MDL Number: MFCD00136047
Linear Formula: C24H41N3O16
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-T2144-10MG 10 mg
 $327.00
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assay ≥93% (HPLC)
color white to yellow cast
form powder
impurities ≤8% water (Karl Fischer)
InChI 1S/C24H41N3O16/c1-8(32)25-11(4-28)17(36)21(12(35)5-29)42-24-16(27-10(3)34)20(39)22(14(7-31)41-24)43-23-15(26-9(2)33)19(38)18(37)13(6-30)40-23/h4,11-24,29-31,35-39H,5-7H2,1-3H3,(H,25,32)(H,26,33)(H,27,34)/t11-,12+,13+,14+,15+,16+,17+,18+,19+,20+,21+,22+,23-,24-/m0/s1
InChI key LRDDKCYRFNJZBX-WHFMPQCRSA-N
Quality Level 200 
SMILES string CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H](O)[C@H]1NC(C)=O)[C@H](O)CO
solubility water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp. −20°C
Application: N,N′,N′′-Triacetylchitotriose has been used:
• as a competitive inhibitor of the enzymatic activity of lysozyme to treat Macrophages to inhibit the constitutively lysozyme production
• to dock the catalytic cleft of Cel9A (endocellulases)
• as an inhibitory sugar to access the specificity of labelling with gold complexed lectin
Biochem/physiol Actions: N,N′,N′′-Triacetylchitotriose is a chitin oligosaccharide, that promotes lysozyme inhibition. Chitin oligosaccharides are associated with many physiological functions. They are biodegradable and are useful in identifying chitin polysaccharides and associated glycoconjugates.
Other Notes: To gain a comprehensive understanding of our extensive range of Oligosaccharides  for your research, we encourage you to visit our Carbohydrates  Category page.
Packaging: 10, 50 mg in glass bottle
Preparation Note: Prepared by the method of Barker, S.A., et al., J. Chem. Soc., 2218 (1958).
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥93% (HPLC)
Storage Temp. −20°C
UNSPSC 12352201

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