N-[(3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide

• ChemBase编号: 154056
• 分子式: C8H16N2O4
• 平均质量: 204.22364
• 单一同位素质量: 204.111007
• SMILES: CC(=O)N[C@H]1CN[C@@H]([C@H]([C@@H]1O)O)CO
• Canonical SMILES: OC[C@H]1NC[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H16N2O4/c1-4(12)10-5-2-9-6(3-11)8(14)7(5)13/h5-9,11,13-14H,2-3H2,1H3,(H,10,12)/t5-,6+,7+,8+/m0/s1
• InChIKey: GBRAQQUMMCVTAV-LXGUWJNJSA-N

名称和登记号

名称

• IUPAC标准名: N-[(3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide
• IUPAC传统名: N-[(3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide
• 别名: 2-Acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol; 2-Acetamido-1,2-dideoxynojirimycin; N-[(3S,4R,5R,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-piperidinyl]acetamide; 2-Acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol; 2-Acetamido-1,2-dideoxynojirimycin

登记号

• CAS号: 105265-96-1
• PubChem SID: 162248195
• PubChem CID: 122617

理论计算性质

• Acid pKa: 13.125802
• 质子受体: 5
• 质子供体: 5
• LogD (pH = 5.5): -5.4755797
• LogD (pH = 7.4): -3.7568586
• Log P: -3.1737783
• 摩尔折射率: 47.6757 cm^3
• 极化性: 19.456116 Å^3
• 极化表面积: 101.82 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White Solid
• 熔点: 227-228°C

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: 36/37/38
• 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-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C8H16N2O4

详细说明

Sigma Aldrich - 90921

Application
2-Acetamido-1,2-dideoxynojirimycin (2-ADN) is used as an inhibitor (transition analogue) to identify, purify, differentiate and characterized N-acetylglucosaminidase(s) (GlcNAcase). 2-Acetamido-1,2-dideoxynojirimycin is used as a ligand for the affinity purification of N-acetylglucosaminidases.

Toronto Research Chemicals - A158400

An analogue of deoxynojirimycin, was found to be a potent inhibitor of a number of N-acetylglucosaminidases.

参考文献

• Tropak, M., et al.: J. Biol. Chem., 279, 13478 (2004)
• Mega, T., et al.: J. Biochem., 136, 525 (2004)
• Greimel, P., et al.: Bioorg. Med. Chem. Lett., 16, 2067 (2004)
• Gutternigg, M., et al.: J. Biol. Chem., 282, 27825 (2004)