T2144

N,N′,N′′-Triacetylchitotriose

≥93% (HPLC)

• Synonym(s): 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
• Empirical Formula (Hill Notation): C₂₄H₄₁N₃O₁₆
• CAS Number: 38864-21-0
• Molecular Weight: 627.59
• UNSPSC Code: 12352201
• NACRES: NA.25
• PubChem Substance ID: 24900018
• MDL number: MFCD00136047
• Beilstein/REAXYS Number: 75249

Properties

• Quality Segment: 200
• assay: ≥93% (HPLC)
• form: powder
• impurities: ≤8% water (Karl Fischer)
• color: white to yellow cast
• solubility: water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
• storage temp.: −20°C
• 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
• 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

Description

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.

Preparation Note

Prepared by the method of Barker, S.A., et al., J. Chem. Soc., 2218 (1958).

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)