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Merck
CN

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

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About This Item

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

Key Documents

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Product Name

N,N′,N′′-Triacetylchitotriose, ≥93% (HPLC)

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

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 key

LRDDKCYRFNJZBX-WHFMPQCRSA-N

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

Quality Level

200

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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.

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.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000452302
0000452302
0000441395
0000441395
0000395835

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Analysis of chitin oligosaccharides by capillary electrophoresis with laser-induced fluorescence
Wang CY and Hsieh YZ
Journal of Chromatography A, 979(1-2), 431-438 (2002)
Isolation and immunolocalization of a Pinus nigra lectin (PNL) during interaction with the necrotrophs?Heterobasidion annosum and Fusarium avenaceum
Nahalkova J, et al.
Physiological and Molecular Plant Pathology, 59(3), 153-163 (2001)
Lysozyme plays a dual role against the dimorphic fungus Paracoccidioides brasiliensis
Lopera D, et al.
Revista Do Instituto De Medicina Tropical De Sao Paulo, 50(3), 169-175 (2008)
Chitin binding by Thermobifida fusca cellulase catalytic domains
Li Y and Wilson DB
Biotechnology and Bioengineering, 100(4), 644-652 (2008)
Sonya M Clark et al.
Analytical chemistry, 76(23), 7077-7083 (2004-12-02)
A novel approach for the quantification of ligand-protein interactions is presented. Electrospray ionization mass spectrometry (ESI-MS) is used to monitor the diffusion behavior of noncovalent ligands in the presence of their protein receptors. These data allow the fraction of free
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