N,N'-Diacetylchitobiose Chemical Properties

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

pka

12.85±0.20(Predicted)

form 

Solid

color 

White to Pale Yellow

optical activity

+32.3 → +16.0

BRN 

61689

Stability:

Hygroscopic

InChIKey

CDOJPCSDOXYJJF-CBTAGEKQSA-N

LogP

-1.870 (est)

CAS DataBase Reference

35061-50-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

3

F 

10

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

N,N'-Diacetylchitobiose Usage And Synthesis

Chemical Properties

White Solid

Uses

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

Uses

lectin inhibitor, immunopotentiator

Uses

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.

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.]

N,N'-Diacetylchitobiose(35061-50-8)Related Product Information

• N,N',N''-TRIACETYLCHITOTRIOSE
• N,N',N'',N''',N'''',N'''''-Hexaacetylchitohexaose
• N,N'-Diacetylchitobiose
• 2-Deoxy-D-glucose
• N-Acetyl-D-Glucosamine
• Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-b-D-gluco- pyranosyl)-2-deoxy-6-O-(a-L-fucopyranosyl)-b-D-glucopyranoside
• P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE
• 4-METHYLUMBELLIFERYL-N,N',N''-TRIACETYL-BETA-CHITOTRIOSIDE
• 4-METHYLUMBELLIFERYL BETA-D-N,N',N',N''-TETRAACETYLCHITOTETRAOSIDE
• N',N'',N''',N''''-Pentaacetylchitopentaose
• D-ALPHA-CHITOBIOSE OCTAACETATE
• GMDP
• P-NITROPHENYL BETA-D-N,N',N''-TRIACETYLCHITOTRIOSE
• BENZYL N,N'-DIACETYL-B-CHITOBIOSIDE
• 4-METHYLUMBELLIFERYL BETA-D-N,N'-DIACETYL-CHITOBIOSIDE
• Methyl 2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-b-D-glucopyranosyl)-2-deoxy-b-D-glucopyranoside
• N',N'',N'''-Tetraacetylchitotetraose
• 8-ETHOXYCARBONYLOCTYL N,N'-DIACETYL-BETA-CHITOBIOSIDE