N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 133011
• Molecular Formular: C16H28N2O11
• Molecular Mass: 424.40032
• Monoisotopic Mass: 424.16930973
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@@H]1[C@H](OC([C@@H]([C@H]1O)NC(=O)C)O)CO)CO)O)O
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1NC(=O)C)O)O)O)NC(=O)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 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; N,N′-Diacetylchitobiose; 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-D-glucose; Bis(N-acetyl)chitobiose; Chitobiose Diacetate; N,N’-Diacetyl-D-chitobiose; N,N'-Diacetylchitobiose

Database IDs

• CAS Number: 35061-50-8
• MDL Number: MFCD00077715
• Beilstein Number: 61689
• PubChem SID: 162227288; 24893467
• PubChem CID: 439544

CALCULATED PROPERTIES

• Acid pKa: 11.504834
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -5.2794456
• LogD (pH = 7.4): -5.279478
• Log P: -5.279445
• Molar Refractivity: 90.5393 cm^3
• Polarizability: 37.461098 Å^3
• Polar Surface Area: 207.27 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless; Methanol; Water
• Apperance: White Solid
• Melting Point: >215°C (dec.); 245-247 °C(lit.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC); ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C16H28N2O11

DETAILS

Sigma Aldrich - D1523

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).
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. Chitobiose is used to study and differentiate chitobiose transporter systems and enzymes such as β-N-acetylglucosaminidase(s) and chitobiose phosphorylase(s).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D1523.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 31538

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.
Other Notes
Binding characteristics of N-acetylglucosamine-specific lectin on isolated chicken hepatocytes1; Characterization of a chito-oligosaccharide-specific lectin from the exudate of ridge gourd2
Preparation Note
by the procedure of S.A. Barker et al., J. Chem. Soc. 2218 (1958)

Toronto Research Chemicals - D310500

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

REFERENCES

• Lefer, A., et al.: Am. J. Physiol., 213, 492 ( 1967), Parrillo, J., et al.: J. Clin. Invest., 76, 1539 (1985)
• Mink, S., et al.: J. Mol. Cell. Cardiol ., 35, 265 (1985)