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Ac-muramic acid

(Synonyms: N-乙酰胞壁酸) 目录号 : GA20621 复制 一键复制产品信息

Ac-muramic acid (N-acetylmuramic acid, MurNAc) 是一种普遍存在的细菌细胞壁糖,其C3位带有独特的D-乳醚取代基。

Ac-muramic acid Chemical Structure

Cas No.:10597-89-4

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100mg
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500mg
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1g
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Description

Ac-muramic acid (N-acetylmuramic acid, MurNAc) is a ubiquitous bacterial cell wall sugar that carries a unique D-lactyl ether substituent at the C3 position [1]. Ac-muramic acid was used as a substrate for Ac-muramic acid etherase MurQ [1]. Ac-muramic acid was obtained either from the environment or from the endogenous cell wall (i.e., recycling). High-level expression of MurQ is required for growth on Ac-muramic acid as the sole source of carbon and energy, whereas constitutive low-level expression of MurQ is sufficient for the recycling of peptidoglycan fragments continuously released from the cell wall during bacterial growth [2].

In vitro, Ac-muramic acid (0-300μg/mL) concentration-dependently inhibited the iNOS and COX-2 protein and mRNA expression in RAW 264.7 cells [3].

In vivo, Ac-muramic acid (40mg/kg; oral gavage; 25 days) inhibited the intestinal villi edema in the E. coli-induced ICR mice and decreased the production of IFN-α in the blood [3].

References:
[1] Jaeger, Tina, Momo Arsic, and Christoph Mayer. "Scission of the lactyl ether bond of N-acetylmuramic acid by Escherichia coli “etherase”." Journal of Biological Chemistry 280.34 (2005): 30100-30106.
[2] Jaeger, Tina, and Christoph Mayer. "The transcriptional factors MurR and catabolite activator protein regulate N-acetylmuramic acid catabolism in Escherichia coli." Journal of bacteriology 190.20 (2008): 6598-6608.
[3] Wu, Zhen, et al. "N-acetylmuramic acid triggers anti-inflammatory capacity in LPS-induced RAW 264.7 cells and mice." journal of functional foods 13 (2015): 108-116.

Ac-muramic acid (N-acetylmuramic acid, MurNAc) 是一种普遍存在的细菌细胞壁糖,其C3位带有独特的D-乳醚取代基[1]。Ac-muramic acid被用作Ac-muramic acid醚酶MurQ的底物[1]。Ac-muramic acid来源于环境或内源细胞壁(即循环利用)。在以Ac-muramic acid作为唯一碳源和能量来源时,细菌需要高水平表达 MurQ才能维持正常生长,而在细菌生长过程中持续从细胞壁释放的肽聚糖片段的回收,仅需 MurQ的组成型低水平表达即可满足[2]

在体外,Ac-muramic acid(0-300μg/mL)呈浓度依赖性地抑制RAW 264.7细胞中iNOS和COX-2蛋白及mRNA的表达[3]

在体内,Ac-muramic acid(40mg/kg;灌胃;25天)抑制大肠杆菌诱导的ICR小鼠肠绒毛水肿,并降低血液中IFN-α水平[3]

实验参考方法

Cell experiment [1]:

Cell lines

RAW 264.7 cells

Preparation Method

RAW 264.7 cells (3 × 105 cells/mL) were seeded into 12-well plates with 1mL DMEM media containing 10% (v/v) FBS. Cells were pretreated with peptidoglycan (PGN), PGN hydrolysate (hydrolyzed by lysozyme at 37°C, 4h), Ac-muramic acid, (N-acetylglucosamine) NAG and tetrapeptides Ala-Glu-Lys-Ala (AEKA) for 4 hours before stimulated with 100ng/mL LPS. Cells were continually cultured for 18 hours for iNOS, COX-2 and GAPDH detection or 30 in for p-p38, IκBα, p-IκBα detection.

Reaction Conditions

0-300μg/mL; 4h

Applications

Ac-muramic acid concentration-dependent inhibited the expressing on iNOS and COX-2 protein expression, from a concentration of 100μg/mL to 300μg/mL.
Animal experiment [1]:

Animal models

Adult male ICR mice

Preparation Method

The control group was orally given a control diet (normal saline alone); three Ac-muramic acid treatment groups (induced by E. coli 0111:B4) (I, II, III) were given Ac-muramic acid doses of 10 (I), 20 (II) and 40 (III) mg·kg−1·d−1 body weight, respectively.

Dosage form

10, 20, 40mg·kg−1·d−1; oral gavage; 25 days

Applications

Ac-muramic acid inhibited the intestinal villi edema in E. coli-induced group.

References:
[1]. Wu, Zhen, et al. "N-acetylmuramic acid triggers anti-inflammatory capacity in LPS-induced RAW 264.7 cells and mice." journal of functional foods 13 (2015): 108-116.

化学性质

Cas No. 10597-89-4 SDF
别名 N-乙酰胞壁酸
分子式 C11H19NO8 分子量 293.27
溶解度 DMF: 2.5 mg/ml,DMSO: 30 mg/ml,PBS (pH 7.2): 10 mg/ml 储存条件 Store at -20°C
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1 mM 3.4098 mL 17.0491 mL 34.0983 mL
5 mM 682 μL 3.4098 mL 6.8197 mL
10 mM 341 μL 1.7049 mL 3.4098 mL
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