D1523
N,N′-Diacetylchitobiose
≥96% (HPLC)
别名:
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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关于此项目
经验公式（希尔记法）:
C16H28N2O11
化学文摘社编号:
分子量:
424.40
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
61689
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
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 key
CDOJPCSDOXYJJF-CBTAGEKQSA-N
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
Quality Level
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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. 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 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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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
Paula Berton et al.
Carbohydrate polymers, 199, 228-235 (2018-08-26)
Chitin, one of Nature's most abundant biopolymers, can be obtained by either traditional chemical pulping or by extraction using the ionic liquid (IL) 1-ethyl-3-methylimidazolium acetate. The IL extraction and coagulation process provides access to a unique chitin, with an open
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