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Teicoplanin

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Identification
Molecular formula
C88H97Cl2N9O33
CAS number
61036-62-2
IUPAC name
3-[[3-acetamido-4-[(6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)oxymethyl]-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]methoxymethyl]-6-[[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]methoxy]-4,5-dihydroxy-5-methyl-tetrahydropyran-2-carboxylic acid
State
State

Teicoplanin is a solid at room temperature. It is used predominantly in powdered form for clinical applications.

Melting point (Celsius)
0.00
Melting point (Kelvin)
0.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
1879.65g/mol
Molar mass
0.0000g/mol
Density
1.5000g/cm3
Appearence

Teicoplanin typically appears as a white to off-white powder. It is a glycopeptide antibiotic complex, consisting of several related compounds, known as teicoplanin factors. These factors are natural products derived from the bacterium Actinoplanes teichomyceticus.

Comment on solubility

Solubility Characteristics

The solubility of 3-[[3-acetamido-4-[(6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)oxymethyl]-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]methoxymethyl]-6-[[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]methoxy]-4,5-dihydroxy-5-methyl-tetrahydropyran-2-carboxylic acid (C88H97Cl2N9O33) is influenced by a variety of factors due to its complex structure. Here are some key points regarding its solubility:

  • Hydrophilic Groups: The presence of multiple hydroxyl (-OH) and carboxylic acid (-COOH) groups suggests that the compound may exhibit reasonable solubility in polar solvents, particularly water.
  • Nonpolar Characteristics: Despite its hydrophilicity, the large hydrophobic regions in the tetrahydropyran rings could limit solubility to some extent, especially in nonpolar solvents.
  • Solvent Dependence: The solubility may vary significantly between different solvents. For instance, solvents like methanol and ethanol may enhance solubility due to their ability to interact with the polar functional groups.
  • pH Sensitivity: The carboxylic acid group can dissociate at higher pH levels, potentially increasing solubility in alkaline environments while reducing it in acidic conditions.

In summary, while this compound is likely to demonstrate moderate to high solubility in polar solvents due to its functional groups, its solubility profile may be complex and dependent on specific environmental factors such as solvent choice and pH.

Interesting facts

Interesting Facts about 3-[[3-acetamido-4-[(6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)oxymethyl]-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]methoxymethyl]-6-[[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]methoxy]-4,5-dihydroxy-5-methyl-tetrahydropyran-2-carboxylic acid

This complex compound, often referred to as a glycosylated derivative, showcases the fascinating versatility of carbohydrates in medicinal chemistry. Glycosylation, in which carbohydrate molecules attach to proteins or lipids, plays a critical role in various biological processes. Here are some engaging insights about this compound:

  • Biological Significance: Compounds like this one are often studied for their potential use in drug development, particularly as anti-inflammatory or immunomodulatory agents.
  • Sugar Moieties: The presence of multiple tetrahydropyran structures highlights the compound's complexity, hinting at its possible interactions with cellular receptors.
  • Acetamido Groups: These functional groups can enhance the solubility and bioavailability of the compound, making it interesting for pharmacological applications.
  • Research Applications: Scientists are exploring such compounds in the treatment of metabolic disorders, given their structural resemblance to naturally occurring sugars.
  • Multifunctionality: The diverse range of hydroxy and carboxylic acid functionalities indicates the potential for numerous chemical reactions, making it a valuable compound for synthetic chemists.

As stated by renowned chemists, “The complexity of a molecule often reflects its potential.” This compound is a testimony to that adage—its intricate structure signifies both a challenge and an opportunity for advancement in fields such as medicinal chemistry and biochemistry.

Overall, this compound exemplifies how intricate carbohydrate chemistry can lead to significant advancements in health-related domains, inviting continuous research and innovation.

Synonyms
Etamucine
CHEBI:231246
3-[[3-acetamido-4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxymethyl]-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]methoxymethyl]-6-[[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]methoxy]-4,5-dihydroxy-5-methyloxane-2-carboxylic acid