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Key Documents

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:
Molecular Weight:
627.59
Beilstein:
75249
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Chitin binding by Thermobifida fusca cellulase catalytic domains
Li Y and Wilson DB
Biotechnology and Bioengineering, 100(4), 644-652 (2008)
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)
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)
Giorgio Colombo et al.
Carbohydrate research, 339(5), 985-994 (2004-03-11)
Herein we study, through all atom molecular dynamics simulations, the complex between hevein and two N-acetylated chitin oligomers, namely N,N(')-diacetylchitobiose and N,N('),N(")-triacetylchitotriose. The results of the simulations for two disaccharide complexes and one trisaccharide complex show that a carbohydrate oligomer

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