Click N-Acetylmuramic acid - alkyne

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Cat.No. 6798 - Click N-Acetylmuramic acid - alkyne | C14H21NO8 | CAS No. 2245794-65-2
Description: Bacterial peptidoglycan derivative; suitable for 'click'-conjugation to fluorescent dyes
Chemical Name: (2R)-2-(((3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-3-(pent-4-ynamido)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid
Purity: ≥97% (HPLC)
Literature (1)

Biological Activity

Derivative of 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.

Technical Data

M. Wt 331.32
Formula C14H21NO8
Storage Store at -20°C
Purity ≥97% (HPLC)
CAS Number 2245794-65-2
Smiles C[C@H](C(O)=O)O[C@H]1[C@@H]([C@H](OC([C@@H]1NC(CCC#C)=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

Solvent Max Conc. mg/mL Max Conc. mM
water 33.13 100

Preparing Stock Solutions

The following data is based on the product molecular weight 331.32. 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
1 mM 3.02 mL 15.09 mL 30.18 mL
5 mM 0.6 mL 3.02 mL 6.04 mL
10 mM 0.3 mL 1.51 mL 3.02 mL
50 mM 0.06 mL 0.3 mL 0.6 mL

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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

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

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Citations for Click N-Acetylmuramic acid - alkyne

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