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HomeProduct name listN,N'-Diacetylchitobiose

N,N'-Diacetylchitobiose

Synonym(s):2-Acetamido-2-deoxy-4-O-(2-acetamido-2-deoxy-β-D-gluco-pyranosyl)-D-glucopyranose;4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-glucose;Chitobiose

N,N'-Diacetylchitobiose Structural

What is N,N'-Diacetylchitobiose?

Chemical properties

White Solid

The Uses of N,N'-Diacetylchitobiose

lectin inhibitor, immunopotentiator

The Uses of N,N'-Diacetylchitobiose

An inhibitor of lysozyme, reverses myocardial depression and lessens norepinephrine requirements in Escherichia coli sepsis in dogs.

The Uses of N,N'-Diacetylchitobiose

Diacetylchitobiose/Chitobiose, a dimer of β(1,4) linked N-acetyl-D glucosamine, is used as an alternative source of N-acetylglucosamine by some bacteria. It is used in fermentation research to study, differentiate and characterize chitobiose transporter systems and enzymes such as β-N-acetylglucosaminidase(s) and chitobiose phosphorylase(s).

Definition

ChEBI: N,N'-diacetylchitobiose is the N,N'-diacetylated derivative of chitobiose, but with no stereodesignation for the anomeric carbon atom. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a beta-D-glucosaminyl-(1->4)-D-glucosamine.

What are the applications of Application

N,N′-Diacetylchitobiose is a major breakdown product of chitinase and smallest substance that induces chitinase

Biochem/physiol Actions

In chitinolytic bacteria, such as Vibrio, Streptomyces and Serratia, N,N′-Diacetylchitobiose (GlcNAc2) is not only a major breakdown product of chitinase, but it is also the smallest substance that induces chitinase production. It can also be utilized as a carbon source by E. coli, which does not express chitinases, but is exposed to GlcNAc2 produced by intestinal chitinolytic bacteria. In most organisms, the uptake of GlcNAc2 occurs via the phosphoenolpyruvate:glycose phosphotransferase system (PTS). GlcNAc2 has also been used as a substrate or inhibitor to study the activity of glycolytic enzymes.

Purification Methods

Recrystallise N,N'-Diacetylchitobiose from aqueous MeOH or aqueous EtOH/1,2-dimethoxyethane. [Zilliken et al. J Chem Soc 77 1296 1955, Beilstein 18/11 V 147.]

Properties of N,N'-Diacetylchitobiose

Melting point: 245-247 °C(lit.)
Boiling point: 927.7±65.0 °C(Predicted)
alpha  18.5 - 39.5 º (c=1% in H2O)
Density  1.50±0.1 g/cm3(Predicted)
storage temp.  −20°C
solubility  H2O: 50 mg/mL, clear, colorless
form  Solid
pka 12.85±0.20(Predicted)
color  White to Pale Yellow
BRN  61689
Stability: Hygroscopic
CAS DataBase Reference 35061-50-8(CAS DataBase Reference)

Safety information for N,N'-Diacetylchitobiose

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for N,N'-Diacetylchitobiose

InChIKey CDOJPCSDOXYJJF-CBTAGEKQSA-N

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