(2R)-2-{[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid

• ChemBase编号: 133311
• 分子式: C11H19NO8
• 平均质量: 293.27046
• 单一同位素质量: 293.11106657
• SMILES: C[C@H](C(=O)O)O[C@H]([C@H](C=O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O[C@@H](C(=O)O)C)NC(=O)C
• InChI: InChI=1S/C11H19NO8/c1-5(11(18)19)20-10(9(17)8(16)4-14)7(3-13)12-6(2)15/h3,5,7-10,14,16-17H,4H2,1-2H3,(H,12,15)(H,18,19)/t5-,7+,8-,9-,10-/m1/s1
• InChIKey: SOARVSUSWULNDI-TVVSKHENSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-{[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid
• IUPAC传统名: N-acetylmuramic acid
• 别名: 2-乙酰胺基-2-脱氧-3-O-(D-1-羧基乙基)-D-吡喃葡萄糖; N-乙酰基-2-葡糖胺-3-乳酸醚; N-乙酰胞壁酸; (+)-N-乙酰胞壁酸; (R)-2-(Acetylamino)-3-O-(1-carboxyethyl)-2-deoxy-D-glucose; 2-Acetamido-2-deoxy-3-O-(D-1-carboxyethyl)-D-glucopyranose; MurNAc; NAMA; N-Acetylmuramic acid; N-Acetylmuramic acid; (+)-N-Acetylmuramic acid

登记号

• CAS号: 10597-89-4
• MDL号: MFCD00221511
• Beilstein号: 1994245
• PubChem SID: 162227588; 24890714
• PubChem CID: 82756

理论计算性质

• Acid pKa: 3.597563
• 质子受体: 8
• 质子供体: 5
• LogD (pH = 5.5): -5.0642366
• LogD (pH = 7.4): -6.5104427
• Log P: -3.1665218
• 摩尔折射率: 63.7766 cm^3
• 极化性: 25.701426 Å^3
• 极化表面积: 153.39 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: ~125 °C (dec.); 125 °C (dec.)(lit.)
• 比旋光度: [α]20/D +41±2°, 24 hr, c = 1.5% in H2O; [α]23/D +65°, c = 0.1 in H2O

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 20/21/22-39/23/24/25
• 安全公开号: 22-35-36/37; 36/37
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H370
• GHS警示性声明: P260-P307 + P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98%; ≥99.0% (TLC); 97%
• 杂质: ≤1 mol/mol methanol
• Empirical Formula (Hill Notation): C11H19NO8

详细说明

Sigma Aldrich - A3007

包装
10, 50, 100, 500 mg in glass bottle
Application
N-Acetylmuramic acid (NAMA), a lactic acid ether derivative of N-acetylglucosamine found in bacterial cell wall proteoglycans, is used as a substrate to identify, differentiate and characterize N-acetylmuramic acid/N-acetylglucosamine kinase(s) and N-acetylmuramic acid etherase(s).

Sigma Aldrich - 01355

Other Notes
MurNAc inhibits the adsorbtion of the bactriocin smegmatocin 14468, to intact Mycobacterium diernhoferi ATCC 19340 cells1