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M2503

Sigma-Aldrich

Muramic acid

≥95% (TLC)

Synonym(s):

2-Amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose

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About This Item

Empirical Formula (Hill Notation):
C9H17NO7
CAS Number:
1114-41-6
Molecular Weight:
251.23
Beilstein:
1713780
MDL number:
MFCD00213428
UNSPSC Code:
12352201
PubChem Substance ID:
24896737
NACRES:
NA.25

Assay

≥95% (TLC)

form

powder

optical activity

[α]25/D 95 to 120°, c = 0.26% (w/v) in water

color

white to off-white

mp

153 °C

solubility

water: 20 mg/mL, clear to very slightly hazy, colorless to faintly yellow

storage temp.

−20°C

SMILES string

C[C@@H](O[C@H]([C@@H](N)C=O)[C@H](O)[C@H](O)CO)C(O)=O

InChI

1S/C9H17NO7/c1-4(9(15)16)17-8(5(10)2-11)7(14)6(13)3-12/h2,4-8,12-14H,3,10H2,1H3,(H,15,16)/t4-,5+,6-,7-,8-/m1/s1

InChI key

ZZHZYDXMAKUKNS-OZRXBMAMSA-N

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General description

Muramic acid is a marker for Gram-positive bacteria.

Application

Muramic acid has been used in a study to examine the association of house dust microbial content with cytokine-producing capacity at birth and at 1 year of age. It has also been used in studies to investigate novel bacteria strains isolated from air and soil samples collected from Korea and Thailand.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Mikko Harri Juhani Lappalainen et al.
International archives of allergy and immunology, 159(2), 194-203 (2012-06-09)
Exposure to microbes and their components may affect the maturation of the immune system. We examined the association of house dust microbial content with cytokine-producing capacity at birth and at the age of 1 year. Production of TNF-α, IFN-γ, IL-5
Apakorn Songsumanus et al.
International journal of systematic and evolutionary microbiology, 63(Pt 2), 554-559 (2012-04-24)
Strain D10-9-5(T) was isolated from mangrove soil in Samut Sakhon province, Thailand. A polyphasic approach was used to determine the taxonomic position of the strain. The strain presented single rough spores on substrate mycelium and no aerial mycelium. Chemotaxonomic data
Elena A Meshcheryakova et al.
Journal of peptide science : an official publication of the European Peptide Society, 21(9), 717-722 (2015-07-15)
Disaccharide containing unit of peptidoglycan from bacterial cell wall, N-acetyl-d-glucosaminyl-N-acetylmuramyl-l-alanyl-d-glutaminamide (gluсosaminyl-muramyl-dipeptide) registered in Russia as an immunomodulatory drug, is shown to participate in slow equilibrium of α and β anomeric forms. Data of NMR spectra and molecular dynamics indicate that
Jenaniy Jeyakumar et al.
Oral health & preventive dentistry, 18(1), 981-990 (2020-11-21)
To analyze in vitro new formulations with Citrox and chlorhexidine digluconate (CHX) regarding their antibacterial activity against planktonic bacteria and their potential to inhibit biofilm formation or to act on existing biofilms. Five oral health care products with 0.05%-0.5% CHX
Filipa Vaz et al.
Cell reports, 27(8), 2480-2492 (2019-05-23)
In Drosophila, it is thought that peptidoglycan recognition proteins (PGRPs) SA and LC structurally discriminate between bacterial peptidoglycans with lysine (Lys) or diaminopimelic (DAP) acid, respectively, thus inducing differential antimicrobial transcription response. Here, we find that accessibility to PG at
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