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D1523

Sigma-Aldrich

N,N′-Diacetylchitobiose

≥96% (HPLC)

Synonym(s):

2-Acetamido-2-deoxy-4-O-(2-acetamido-2-deoxy-β-D-gluco­pyranosyl)-D-glucopyranose, 4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-glucose, Chitobiose

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10 MG
$379.00

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10 MG
$379.00

About This Item

Empirical Formula (Hill Notation):
C16H28N2O11
CAS Number:
35061-50-8
Molecular Weight:
424.40
Beilstein/REAXYS Number:
61689
MDL number:
MFCD00077715
UNSPSC Code:
12352201
PubChem Substance ID:
24893467
NACRES:
NA.25

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Quality Level

200

assay

≥96% (HPLC)

form

powder

optical activity

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

color

off-white

mp

245-247 °C (lit.)

solubility

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

storage temp.

−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

InChI key

CDOJPCSDOXYJJF-CBTAGEKQSA-N

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Application

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.[1] 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).[2][3]

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.

Preparation Note

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

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000400198
0000400198
0000345590
0000315040
0000225059

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Rubén López-Mondéjar et al.
The FEBS journal, 276(18), 5137-5148 (2009-08-14)
The chitinolytic enzyme machinery of fungi consists of chitinases and beta-N-acetylglucosaminidases. These enzymes are important during the fungal life cycle for degradation of exogenous chitin, which is the second most abundant biopolymer, as well as fungal cell-wall remodelling. In addition
Manoharan Mathiselvam et al.
Carbohydrate research, 380, 37-44 (2013-08-07)
The linkage region, GlcNAcβAsn, is conserved in all eukaryotic N-glycoproteins. As a logical extension of a research endeavor aimed at understanding the structural significance of GlcNAc and Asn as the linkage region constituents, the newer analogs GlcNAcβNHBu and (GlcNAcβ(1-4)GlcNAc)alkanamides have
Ken Hamura et al.
Carbohydrate research, 379, 21-25 (2013-07-13)
Cellobiose phosphorylase (EC 2.4.1.20, CBP) catalyzes the reversible phosphorolysis of cellobiose to α-D-glucose 1-phosphate (Glc1P) and d-glucose. Cys485, Tyr648, and Glu653 of CBP from Ruminococcus albus, situated at the +1 subsite, were mutated to modulate acceptor specificity. C485A, Y648F, and
Ryuichi Masaka et al.
Bioorganic & medicinal chemistry, 18(2), 621-629 (2010-01-09)
Two types of nonspacer- and spacer-N-linked tetravalent glycosides bearing N-acetylglucosamine (GlcNAc), N,N'-diacetylchitobiose [(GlcNAc)(2)] and N-acetyllactosamine (LacNAc) were designed and prepared as glycomimetics. The interactions of wheat germ (Triticum vulgaris) agglutinin (WGA) and coral tree (Erythrina cristagalli) agglutinin (ECA) with a
Estefania O Juárez-Hernández et al.
Scientific reports, 9(1), 2591-2591 (2019-02-24)
There is no structural information about any chitinase synthesized by Bacillus thuringiensis, the most successful microbial insect larvicide used worldwide. In this study, we solved the 3D structure of the chitinase ChiA74 at 2.26 Å. The crystal structure shows that ChiA74
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