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编号: 133011
• 分子式: C16H28N2O11
• 平均质量: 424.40032
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: 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
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 11.504834
• 质子受体: 11
• 质子供体: 8
• LogD (pH = 5.5): -5.2794456
• LogD (pH = 7.4): -5.279478
• Log P: -5.279445
• 摩尔折射率: 90.5393 cm^3
• 极化性: 37.461098 Å^3
• 极化表面积: 207.27 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: soluble50 mg/mL, clear, colorless; Methanol; Water
• 外观: White Solid
• 熔点: >215°C (dec.); 245-247 °C(lit.)

安全信息

• 保存条件: -20°C Freezer
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

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

详细说明

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.

参考文献

• 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)