Click N-Acetylmuramic acid - azide

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Description: Bacterial peptidoglycan derivative; suitable for 'click'-conjugation to fluorescent dyes
Chemical Name: (2R)-2-(((3R,4R,5S,6R)-3-(2-Azidoacetamido)-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid
Purity: ≥95% (HPLC)

Biological Activity for Click N-Acetylmuramic acid - azide

Click N-Acetylmuramic acid-azide is a derivative of the N-acetylmuramic acid (NAM) component of bacterial peptidoglycans. Incorporated into bacterial peptidoglycans during biosynthesis. Suitable for fluorescent labeling of peptidoglycans when ''click'-conjugated to a fluorescent dye.

Licensing Information

Sold under license from the University of Delaware

Technical Data for Click N-Acetylmuramic acid - azide

M. Wt 334.29
Formula C11H18N4O8
Storage Store at -20°C
Purity ≥95% (HPLC)
CAS Number 2245794-64-1
Smiles C[C@H](C(O)=O)O[C@H]1[C@@H]([C@H](OC([C@@H]1NC(CN=[N+]=[N-])=O)O)CO)O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for Click N-Acetylmuramic acid - azide

Solvent Max Conc. mg/mL Max Conc. mM
water 1.67 5

Preparing Stock Solutions for Click N-Acetylmuramic acid - azide

The following data is based on the product molecular weight 334.29. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.05 mM 59.83 mL 299.14 mL 598.28 mL
0.25 mM 11.97 mL 59.83 mL 119.66 mL
0.5 mM 5.98 mL 29.91 mL 59.83 mL
2.5 mM 1.2 mL 5.98 mL 11.97 mL

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Product Datasheets for Click N-Acetylmuramic acid - azide

References for Click N-Acetylmuramic acid - azide

References are publications that support the biological activity of the product.

Liang et al (2017) Metabolic labelling of the carbohydrate core in bacterial peptidoglycan and its applications. Nat. Commun. 8 15015 PMID: 28425464

DeMeester et al (2018) Synthesis of functionalized N-acetyl muramic acids to probe bacterial cell wall recycling and biosynthesis. J.Am.Chem.Soc. 140 9458 PMID: 29986130

Wodzanowski et al (2020) Tools for probing host-bacteria interactions in the gut microenvironment: from molecular to cellular levels. Bioorg.Med.Chem.Lett. 30 127116 PMID: 32223923

Wodzanowski et al (2022) Multiscale invasion assay for probing macrophage response to gram-negative bacteria. Front.Chem. 10 842602 PMID: 35242744

Taylor et al (2021e) Localizing peptidoglycan synthesis in helicobacter pylori using clickable metabolic probes. Curr.Protoc. 1 e80 PMID: 33844460

If you know of a relevant reference for Click N-Acetylmuramic acid - azide, please let us know.

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Citations for Click N-Acetylmuramic acid - azide

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