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Merck
CN

T2144

N,N′,N′′-Triacetylchitotriose

≥93% (HPLC)

别名:

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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关于此项目

经验公式（希尔记法）:
C24H41N3O16
化学文摘社编号:
38864-21-0
分子量:
627.59
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24900018
MDL number:
MFCD00136047
Beilstein/REAXYS Number:
75249

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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

相关类别

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000452302
0000452302
0000441395
0000441395
0000395835

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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)
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)
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)
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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