N,N',N''-TRIACETYLCHITOTRIOSE Chemical Properties

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

pka

12.72±0.70(Predicted)

form 

Solid

color 

White to Pale Beige

BRN 

75249

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

10-21

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

N,N',N''-TRIACETYLCHITOTRIOSE Usage And Synthesis

Chemical Properties

Off-White Crystalline Solid

Uses

N,N’,N’’-Triacetyl Chitotriose is a multivalent glycosides with strong crosslinking activity for lectin as a specific coagulant.

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.

Definition

ChEBI: Tri-N-acetylchitotriose is a N-acyl-hexosamine.

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.

1. Hydrolysis of 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside by lysozyme and its inhibition by N,N',N''-triacetylchitotriose
2. Tanimoto; Fukuda; Kawamura - Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 9, p. 3607 - 361

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