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Key Documents

A3007

Sigma-Aldrich

N-Acetylmuramic acid

≥98% (TLC)

Synonym(s):

(R)-2-(Acetylamino)-3-O-(1-carboxyethyl)-2-deoxy-D-glucose, 2-Acetamido-2-deoxy-3-O-(D-1-carboxyethyl)-D-glucopyranose, MurNAc, NAMA

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About This Item

Empirical Formula (Hill Notation):
C11H19NO8
CAS Number:
Molecular Weight:
293.27
Beilstein:
1994245
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic

Assay

≥98% (TLC)

form

powder

technique(s)

thin layer chromatography (TLC): suitable

impurities

≤1 mol/mol methanol

color

white

mp

125  °C ((257 °F ))

solubility

water: 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

CC(O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O)C(O)=O

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

InChI key

SOARVSUSWULNDI-TVVSKHENSA-N

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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).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 2

Target Organs

Eyes,Central nervous system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Markus B Tomek et al.
Frontiers in microbiology, 9, 2008-2008 (2018-09-14)
The cell surface of the oral pathogen Tannerella forsythia is heavily glycosylated with a unique, complex decasaccharide that is O-glycosidically linked to the bacterium's abundant surface (S-) layer, as well as other proteins. The S-layer glycoproteins are virulence factors of
Marta Kamińska et al.
Journal of periodontology, 90(6), 637-646 (2018-12-07)
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Kanda Leelanarathiwat et al.
The International journal of oral & maxillofacial implants, 35(2), 265-274 (2020-03-07)
Peri-implantitis is an important biologic complication that can lead to implant failure. Proper treatment should effectively kill bacteria, not harm the implant surface, and promote regeneration. Recently, photocatalytic coating without antibiotics or external agents was proposed to be an alternative
Wentao Jiang et al.
Applied and environmental microbiology, 86(14) (2020-05-18)
Due to the complex microecology and microenvironment of dental plaque, novel caries prevention strategies require modulating the microbial communities ecologically and reducing the cariogenic properties effectively. Antimicrobial peptide GH12 reduced the lactic acid production and exopolysaccharide (EPS) synthesis of a
Markus B Tomek et al.
Glycobiology, 27(6), 555-567 (2017-03-24)
The occurrence of nonulosonic acids in bacteria is wide-spread and linked to pathogenicity. However, the knowledge of cognate nonulosonic acid transferases is scarce. In the periodontopathogen Tannerella forsythia, several proposed virulence factors carry strain-specifically either a pseudaminic or a legionaminic

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