Muramic acid
(Synonyms: 保护胞壁酸) 目录号 : GC63086
Muramic acid 是许多革兰氏阳性细菌细胞壁中的一种成分，可作为革兰氏阳性细菌的标记物。
Cas No.:1114-41-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Muramic acid is a component in many Gram-positive bacterial cell walls, as marker for Gram-positive bacteria[1].
[1]. Lappalainen MHJ, et, al. High indoor microbial levels are associated with reduced Th1 cytokine secretion capacity in infancy. Int Arch Allergy Immunol. 2012; 159(2): 194-203.
| Cas No. | 1114-41-6 | SDF | |
| 别名 | 保护胞壁酸 | ||
| 分子式 | C9H17NO7 | 分子量 | 251.23 |
| 溶解度 | 储存条件 | Store at 2-8°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.9804 mL | 19.9021 mL | 39.8042 mL |
| 5 mM | 0.7961 mL | 3.9804 mL | 7.9608 mL |
| 10 mM | 0.398 mL | 1.9902 mL | 3.9804 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Protected N-Acetyl Muramic acid Probes Improve Bacterial Peptidoglycan Incorporation via Metabolic Labeling
ACS Chem Biol 2021 Oct 15;16(10):1908-1916.PMID:34506714DOI:10.1021/acschembio.1c00268.
Metabolic glycan probes have emerged as an excellent tool to investigate vital questions in biology. Recently, methodology to incorporate metabolic bacterial glycan probes into the cell wall of a variety of bacterial species has been developed. In order to improve this method, a scalable synthesis of the peptidoglycan precursors is developed here, allowing for access to essential peptidoglycan immunological fragments and cell wall building blocks. The question was asked if masking polar groups of the glycan probe would increase overall incorporation, a common strategy exploited in mammalian glycobiology. Here, we show, through cellular assays, that E. coli do not utilize peracetylated peptidoglycan substrates but do employ methyl esters. The 10-fold improvement of probe utilization indicates that (i) masking the carboxylic acid is favorable for transport and (ii) bacterial esterases are capable of removing the methyl ester for use in peptidoglycan biosynthesis. This investigation advances bacterial cell wall biology, offering a prescription on how to best deliver and utilize bacterial metabolic glycan probes.
Muramic acid as a measure of microbial biomass in estuarine and marine samples
Appl Environ Microbiol 1977 Apr;33(4):777-83.PMID:869528DOI:10.1128/aem.33.4.777-783.1977.
Muramic acid, a component of the muramyl peptide found only in the cell walls of bacteria and blue-green algae, furnishes a measure of detrital or sedimentary procaryotic biomass. A reproducible assay involving acid hydrolysis, preparative thin-layer chromatographic purification, and colorimetric analysis of lactate released from Muramic acid by alkaline hydrolysis is described. Comparison of semitropical estuarine detritus, estuarine muds, and sediments from anaerobic Black Sea cores showed Muramic acid levels of 100 to 700 microng/g (dry weight), 34 microng/g, and 1.5 to 14.9 microng/g, respectively. Enzymatic assays of lactate from Muramic acid gave results 10- to 20-fold higher. Radioactive pulse-labeling studies showed that [14C]acetate is rapidly incorporated into Muramic acid by the detrital microflora. Subsequent loss of 14C, accompanied by nearly constant levels of total Muramic acid, indicated active metabolism in procaryotic cell walls.
Muramic acid measurements for bacterial investigations in marine environments by high-pressure liquid chromatography
Appl Environ Microbiol 1985 Aug;50(2):229-37.PMID:16346848DOI:10.1128/aem.50.2.229-237.1985.
Muramic acid, a constituent of procaryotic cell walls, was assayed by high-pressure liquid chromatography in samples from several marine environments (water column, surface microlayer, and sediment) and a bacterial culture. It is used as a microbial biomass indicator. The method gave a good separation of Muramic acid from interfering compounds with satisfactory reproducibility. A pseudomonad culture had a Muramic acid content of 4.7 x 10 to 5.3 x 10 mug per cell during growth. In natural water samples, highly significant relationships were found between Muramic acid concentrations and bacterial numbers for populations of 10 to 10 cells per liter. The Muramic acid content in natural marine water decreased from 5.3 x 10 to 1.6 x 10 mug per cell with increasing depth. In coastal sediments exposed to sewage pollution, concentrations of Muramic acid, ATP, organic carbon, and total amino acids displayed a parallel decrease with increasing distance from the sewage outlet. Advantages of Muramic acid measurement by high-pressure liquid chromatography are its high sensitivity and reduction of preparation steps, allowing a short time analysis.
Muramic acid, endotoxin, 3-hydroxy fatty acids, and ergosterol content explain monocyte and epithelial cell inflammatory responses to agricultural dusts
J Toxicol Environ Health A 2010;73(10):684-700.PMID:20391112DOI:10.1080/15287390903578539.
In agricultural and other environments, inhalation of airborne microorganisms is linked to respiratory disease development. Bacterial endotoxins, peptidoglycans, and fungi are potential causative agents, but relative microbial characterization and inflammatory comparisons amongst agricultural dusts are not well described. The aim of this study was to determine the distribution of microbial endotoxin, 3-hydroxy fatty acids (3-OHFA), Muramic acid, and ergosterol and evaluate inflammatory responses in human monocytes and bronchial epithelial cells with various dust samples. Settled surface dust was obtained from five environments: swine facility, dairy barn, grain elevator, domestic home (no pets), and domestic home with dog. Endotoxin concentration was determined by recombinant factor C (rFC). 3-OHFA, Muramic acid, and ergosterol were measured using gas chromatography-mass spectrometry. Dust-induced inflammatory cytokine secretion in human monocytes and bronchial epithelial cells was evaluated. Endotoxin-independent dust-induced inflammatory responses were evaluated. Endotoxin and 3-OHFA levels were highest in agricultural dusts. Muramic acid, endotoxin, 3-OHFA, and ergosterol were detected in dusts samples. Muramic acid was highest in animal farming dusts. Ergosterol was most significant in grain elevator dust. Agricultural dusts induced monocyte tumor necrosis factor (TNF) alpha, interleukin (IL)-6, IL-8, and epithelial cell IL-6 and IL-8 secretion. Monocyte and epithelial IL-6 and IL-8 secretion was not dependent on endotoxin. House dust(s) induced monocyte TNFalpha, IL-6, and IL-8 secretion. Swine facility dust generally produced elevated responses compared to other dusts. Agricultural dusts are complex with significant microbial component contribution. Large animal farming dust(s)-induced inflammation is not entirely dependent on endotoxin. Addition of Muramic acid to endotoxin in large animal farming environment monitoring is warranted.
Metabolic Incorporation of N-Acetyl Muramic acid Probes into Bacterial Peptidoglycan
Curr Protoc Chem Biol 2019 Dec;11(4):e74.PMID:31763799DOI:10.1002/cpch.74.
Bacterial cells utilize small carbohydrate building blocks to construct peptidoglycan (PG), a highly conserved mesh-like polymer that serves as a protective coat for the cell. PG production has long been a target for antibiotics, and its breakdown is a source for human immune recognition. A key component of bacterial PG, N-acetyl Muramic acid (NAM), is a vital element in many synthetically derived immunostimulatory compounds. However, the exact molecular details of these structures and how they are generated remain unknown due to a lack of chemical probes surrounding the NAM core. A robust synthetic strategy to generate bioorthogonally tagged NAM carbohydrate units is implemented. These molecules serve as precursors for PG biosynthesis and recycling. Escherichia coli cells are metabolically engineered to incorporate the bioorthogonal NAM probes into their PG network. The probes are subsequently modified using copper-catalyzed azide-alkyne cycloaddition to install fluorophores directly into the bacterial PG, as confirmed by super-resolution microscopy and high-resolution mass spectrometry. Here, synthetic notes for key elements of this process to generate the sugar probes as well as streamlined user-friendly metabolic labeling strategies for both microbiology and immunological applications are described. © 2019 by John Wiley & Sons, Inc. Basic Protocol 1: Synthesis of peracetylated 2-azido glucosamine Basic Protocol 2: Synthesis of 2-azido and 2-alkyne NAM Basic Protocol 3: Synthesis of 3-azido NAM methyl ester Basic Protocol 4: Incorporation of NAM probes into bacterial peptidoglycan Basic Protocol 5: Confirmation of bacterial cell wall remodeling by mass spectrometry.