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T2144

Sigma-Aldrich

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

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About This Item

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

Quality Level

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

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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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