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

• ChemBase ID: 133311
• Molecular Formular: C11H19NO8
• Molecular Mass: 293.27046
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid
• IUPAC Traditional name: N-acetylmuramic acid
• Synonyms: (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; 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.597563
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.0642366
• LogD (pH = 7.4): -6.5104427
• Log P: -3.1665218
• Molar Refractivity: 63.7766 cm^3
• Polarizability: 25.701426 Å^3
• Polar Surface Area: 153.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 20/21/22-39/23/24/25
• Safety Statements: 22-35-36/37; 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H370
• GHS Precautionary statements: P260-P307 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

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

DETAILS

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