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Neomycin

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Identification
Molecular formula
C23H46N6O13
CAS number
1404-04-2
IUPAC name
(2R,3S,4R,5R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1S,2S,3R,5S,6R)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]oxy-tetrahydropyran-3,4-diol
State
State

At room temperature, neomycin is typically in the solid state, especially when isolated as its sulfate salt. As a dry powder, it is stable and can be stored for long durations away from light and moisture.

Melting point (Celsius)
170.20
Melting point (Kelvin)
443.35
Boiling point (Celsius)
253.00
Boiling point (Kelvin)
526.15
General information
Molecular weight
614.63g/mol
Molar mass
614.6340g/mol
Density
1.8000g/cm3
Appearence

Neomycin is typically found as a white to off-white powder. It is hygroscopic, meaning it can readily absorb moisture from the air. Depending on the specific formulation, it can also be part of a colorless to slightly yellowish solution.

Comment on solubility

Solubility of (2R,3S,4R,5R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1S,2S,3R,5S,6R)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]oxy-tetrahydropyran-3,4-diol

The solubility of complex organic compounds like (2R,3S,4R,5R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1S,2S,3R,5S,6R)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]oxy-tetrahydropyran-3,4-diol is often influenced by several key factors:

  • Structural Complexity: The intricate structure of the compound, with multiple functional groups such as amino, hydroxy, and ether, can significantly impact solubility. Compounds with numerous hydroxyl (-OH) groups tend to be more soluble in water due to their ability to form hydrogen bonds.
  • Polarity: The presence of polar functional groups increases the molecule's interaction with polar solvents like water, often enhancing solubility.
  • Steric Effects: The stereochemistry of the compound may create steric hindrance, affecting how it interacts with solvent molecules.
  • pH Sensitivity: The solubility may vary with pH, especially for compounds with amino groups, as these can become protonated in acidic conditions, influencing solubility behavior.

As a general observation, while more hydrophilic molecules can dissolve in aqueous solutions, those that are more lipophilic may require nonpolar solvents for effective solubility. It’s crucial to conduct empirical tests to ascertain the exact solubility characteristics of such complex compounds.

Interesting facts

Exploring the Complex Compound: (2R,3S,4R,5R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1S,2S,3R,5S,6R)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]oxy-tetrahydropyran-3,4-diol

This compound is a fascinating example of *chiral compounds* due to the presence of multiple stereocenters. Chirality plays a crucial role in the biological activity of molecules; therefore, understanding the specific orientation of the atoms in this compound can provide insights into its potential applications. Here are some intriguing aspects to consider:

  • Functional Groups: The compound features various functional groups including amino, hydroxyl, and tetrahydropyran structures, which suggest a rich chemistry that could lead to interesting biochemical interactions.
  • Biological Relevance: Compounds with such complex structures are often of interest in pharmaceutical chemistry as potential drugs or bioactive molecules. The multiple amino and hydroxyl groups may enhance solubility and receptor binding, potentially impacting therapeutic efficacy.
  • Synthesis Challenges: The synthesis of such complex molecules can be a challenge due to their intricate structures. Chemists may employ strategies such as asymmetric synthesis and protecting group techniques to construct these compounds effectively.
  • Natural Product Inspiration: Many complex polysaccharides and glycosides found in nature possess similar structural motifs, indicating that this compound might mimic or interact with biological systems similar to natural molecules.

As a chemistry student, delving into this compound can enhance your understanding of stereochemistry, synthesis techniques, and the relationship between molecular structure and function in biological systems. Additionally, studying such compounds can cultivate a deeper appreciation for the complexities of *molecular interactions*, paving the way for innovations in drug design and development.

In conclusion, exploring compounds like (2R,3S,4R,5R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1S,2S,3R,5S,6R)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]oxy-tetrahydropyran-3,4-diol opens not only doors to fundamental chemistry but also to biochemistry and medicinal applications.