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N-Acetylmuramic acid

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Identification
Molecular formula
C11H19NO8
CAS number
1114-41-6
IUPAC name
4-[[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-amino-4-oxo-butanoic acid
State
State

At room temperature, N-Acetylmuramic acid exists as a solid crystalline substance.

Melting point (Celsius)
192.00
Melting point (Kelvin)
465.15
Boiling point (Celsius)
572.00
Boiling point (Kelvin)
845.15
General information
Molecular weight
295.27g/mol
Molar mass
295.2680g/mol
Density
1.6500g/cm3
Appearence

N-Acetylmuramic acid, commonly known as MurNAc, is typically a white to off-white crystalline solid. It is hygroscopic in nature, meaning it can absorb moisture from the air.

Comment on solubility

Solubility of 4-[[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-amino-4-oxo-butanoic acid

The solubility of this compound, with the chemical formula C11H19NO8, can be influenced by several factors:

  • Polarity: Due to the presence of various hydroxyl (-OH) and acetamido (-NHCOCH3) functional groups, this compound is likely to be polar. Polar compounds typically exhibit better solubility in polar solvents such as water.
  • Hydrogen Bonding: The ability of this compound to form hydrogen bonds can significantly enhance its solubility in aqueous solutions. Hydroxyl groups on the molecule may engage in hydrogen bonding with water molecules, facilitating dissolution.
  • pH Sensitivity: The solubility may also be affected by the pH of the solution, particularly due to the carboxylic acid functional group. At lower pH levels, the acid may remain protonated, impacting its solubility characteristics.
  • Temperature Dependency: Like many organic compounds, the solubility may vary with temperature. Generally, heating can increase solubility, providing a more favorable kinetic environment for interaction with solvents.

In conclusion, while specific solubility data may need to be experimentally determined, understanding the chemical structure and potential interactions can provide valuable insights into the compound's behavior in solution. Thus, it can be anticipated that 4-[[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-amino-4-oxo-butanoic acid will showcase reasonable solubility, especially in polar solvents.

Interesting facts

Interesting Facts about 4-[[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-amino-4-oxo-butanoic acid

This compound is a fascinating example of a multi-functional molecule with biological significance. Here are some key insights into its structure and potential applications:

  • Diverse Functional Groups: The compound features various functional groups, including amino, acetamido, and hydroxyl, which play critical roles in its reactivity and interaction with biological systems.
  • Potential Biological Activity: The unique structural components suggest potential uses in pharmaceuticals, particularly in drug design and development. Compounds with amino acid and sugar moieties can influence metabolic pathways and serve as scaffolds for therapeutic agents.
  • Glycosylation: The presence of a tetrahydropyran ring suggests that this compound may undergo glycosylation processes. Glycosylated compounds are essential in biology as they can modify the behavior of proteins and lipids.
  • Analog to Natural Products: This compound is structurally similar to natural amino sugars, which are vital in a variety of biological functions, including cell signaling, structural integrity of cell walls, and as substrates for enzyme catalysis.
  • Research Potential: The interesting combination of peptide and sugar-like structures offers extensive opportunities for research in the fields of medicinal chemistry and biochemistry.

As scientists delve deeper into the properties and functions of such compounds, they might uncover novel pathways for therapeutic interventions and gain a better understanding of their roles in biological systems. Nature often presents us with complexities that invite exploration and innovation!

Synonyms
4-[[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-amino-4-oxobutanoic acid
AADG;Aspartylglucosamine;N-gamma-(2-Acetamido-2-deoxy-beta-D-gluco-pyranosyl)-L-asparagine
N-Asn
2-acetamido-n-beta-aspartyl-2-deoxyhexopyranosylamine
DTXSID10863022
NS00014891
Ng-(2-Acetamido-2-deoxy-b-D-gluco-pyranosyl)-L-asparagine
2-Acetamido-1-N-(beta-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine, >=98%