| Identification | Back Directory | [Name]
N,N',N''-TRIACETYLCHITOTRIOSE | [CAS]
38864-21-0 | [Synonyms]
CHITOTRIOSE
[(GlcNAc)3]
Tri(N-acetylglucosaMine)
N-acetylated Chitotriose
CHITOTRIOSE, TRI-N-ACETYL
N-AcetylglucosaMine TriMer
N,N',N'-TRIACETYLCHITOTRIOSE
GLCNAC1-B-4GLCNAC1-B-4GLCNAC
N,N',N''-TRIACETYLCHITOTRIOSE
GlcNAcβ(1-4)GlcNAcβ(1-4)GlcNAc
N,N',N''-Triacetylchitotriose ,95%
GLCNAC-BETA1-4GLCNAC-BETA1-4GLCNAC
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
O-[2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL-(1->4)]-O-[2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYR-ANOSYL-(1->4)]-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE
N,N′,N′′-Triacetylchitotriose,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
N-[(2R,3R,4R,5R)-4-[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5,6-trihydroxy-1-oxo-hexan-2-yl]acetamide | [Molecular Formula]
C24H41N3O16 | [MDL Number]
MFCD00136047 | [MOL File]
38864-21-0.mol | [Molecular Weight]
627.59 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Crystalline Solid | [Melting point ]
271-272°C dec. | [Boiling point ]
1146.9±65.0 °C(Predicted) | [density ]
1.54±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
H2O: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
| [form ]
Solid | [pka]
12.72±0.70(Predicted) | [color ]
White to Pale Beige | [Water Solubility ]
water: 50mg/mL, clear to slightly hazy, colorless to faintly yellow | [BRN ]
75249 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Crystalline Solid | [Definition]
ChEBI: Tri-N-acetylchitotriose is a N-acyl-hexosamine. | [Biological Activity]
N,Nμ,Nμμ-Triacetylchitotriose is a chitin oligosaccharideth at promotes lysozyme inhibition. Chitin oligosaccharides are associated with many physiological functions. They are biodegradable and are useful in identifying chitin polysaccharides and associated glycoconjugates. |
| Questions and Answers (Q&A) | Back Directory | [Uses]
N,N',N''-Triacetylchitotriose is a triose oligosaccharide derived from chitin, consisting of three N-acetylglucosamine units. It has been shown to scavenge reactive oxygen species and to protect DNA from oxidative damage.
| [Reactions]
The hydrolytic activity of lysozyme towards 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside (4-MU-(GlcNAc)4) was little affected by ionic strength, though the activity of lysozyme towards cell suspension of Micrococcus lysodeikticus varied markedly with ionic strength. About 40-60percent of lysozyme activity with 4-MU-(GlcNAc)4 as a substrate was inhibited by 0.1 mM N,N',N''-triacetylchitotriose ((GlcNAc)3), but the lytic activity of lysozyme towards M. lysodeikticus was little affected. The kinetics of hydrolysis of 4-MU-(GlcNAc)4 by hen eggwhite (HEW) lysozyme and human placental (HP) lysozyme and the inhibition of this hydrolysis by (GlcNAc)3 were investigated. The K(s) values for 4-MU-(GlcNAc)4 of HEW- and HP-lysozymes were 19.7 and 27.9 μM, respectively, and the V(max) values were 0.124 and 0.0833 nmol/min/mg, respectively. The k values of both enzymes were very low, implying a poor orientation of the scissile bond in the substrate molecule with respect to the active site of lysozyme. (GlcNAc)3 inhibited lysozyme with hyperbolic mixed-type inhibition. The inhibition reduced V(max) values of both lysozymes. The K(s) value of HEW-lysozyme was increased by the addition of the inhibitory whereas the K(s) value of HP-lysozyme was decreased. The K(i) value was 29.6 μm for HEW-lysozyme and 106 μM for HP-lysozyme.
- Hydrolysis of 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside by lysozyme and its inhibition by N,N',N''-triacetylchitotriose
- Tanimoto; Fukuda; Kawamura - Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 9, p. 3607 - 361
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