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
- CAS NO.:35061-50-8
- Empirical Formula: C16H28N2O11
- Molecular Weight: 424.4
- MDL number: MFCD00077715
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-28 13:53:21
What is N,N'-Diacetylchitobiose?
Chemical properties
White Solid
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
lectin inhibitor, immunopotentiator
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).
What are the applications of Application
N,N′-Diacetylchitobiose is a major breakdown product of chitinase and smallest substance that induces chitinase
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.
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) |
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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