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Merck

D1523

Sigma-Aldrich

N,N′-Diacetylchitobiose

≥96% (HPLC)

Synonym(e):

4-O-(2-Acetamino-2-deoxy-β-D-glucopyranosyl)-2-acetamino-2-deoxy-D-glucose

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About This Item

Empirische Formel (Hill-System):
C16H28N2O11
CAS-Nummer:
Molekulargewicht:
424.40
Beilstein:
61689
MDL-Nummer:
UNSPSC-Code:
12352201
PubChem Substanz-ID:
NACRES:
NA.25

Qualitätsniveau

Assay

≥96% (HPLC)

Form

powder

Optische Aktivität

[α]/D 15.00 to 19.00 °, c = 9.00-11.00 mg/mL in water

Farbe

off-white

mp (Schmelzpunkt)

245-247 °C (lit.)

Löslichkeit

H2O: 49.00-51.00 mg/mL, clear, colorless

Lagertemp.

−20°C

SMILES String

CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O

InChI

1S/C16H28N2O11/c1-5(21)17-9-13(25)14(8(4-20)27-15(9)26)29-16-10(18-6(2)22)12(24)11(23)7(3-19)28-16/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)/t7-,8-,9-,10-,11-,12-,13-,14-,15?,16+/m1/s1

InChIKey

CDOJPCSDOXYJJF-CBTAGEKQSA-N

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Anwendung

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).

Biochem./physiol. Wirkung

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.

Angaben zur Herstellung

Prepared by the method of Barker, S.A., et al., J. Chem. Soc., 2218 (1958).

Sonstige Hinweise

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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