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Neomycin

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Identification
Molecular formula
C23H46N6O13
CAS number
1404-04-2
IUPAC name
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R)-5-[(1R,3S,5R,6S)-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 generally in a solid state, often found as a powder or crystalline solid.

Melting point (Celsius)
168.50
Melting point (Kelvin)
441.65
Boiling point (Celsius)
214.00
Boiling point (Kelvin)
487.15
General information
Molecular weight
615.64g/mol
Molar mass
615.6390g/mol
Density
1.6900g/cm3
Appearence

Neomycin is an aminoglycoside antibiotic, typically characterized as a white to off-white powder. It can also be in a crystalline form, which is visually indistinguishable from its powdered state without magnification. Neomycin can be hygroscopic, meaning it tends to absorb moisture from the air.

Comment on solubility

Solubility of (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R)-5-[(1R,3S,5R,6S)-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 this complex compound is influenced by several factors, primarily its intricate molecular structure. Here are some essential points regarding its solubility:

  • Hydrophilicity: The presence of multiple hydroxyl (-OH) and amino (-NH₂) groups typically increases the compound's affinity for water, enhancing its solubility.
  • Structural Configuration: The stereochemistry, indicated by multiple chiral centers, can affect how the molecule interacts with solvents.
  • Potential Interactions: Hydrogen bonding with water molecules can play a significant role in solubility due to the presence of functional groups.
  • Concentration Dependency: The solubility may vary significantly with changes in temperature and pH, which may alter the solvation dynamics.

As a result, the detailed examination of solubility for this compound can be summarized as follows:

  1. The compound is likely to exhibit moderate to high solubility in aqueous solutions.
  2. Solubility may vary in organic solvents, indicating a need for specific solvent choice in practical applications.
  3. It is crucial to consider that the optimal conditions for solubility can be compound-specific.

The intricate nature of (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R)-5-[(1R,3S,5R,6S)-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 underscores the importance of thorough analysis in understanding its solubility characteristics.

Interesting facts

Interesting Facts about (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R)-5-[(1R,3S,5R,6S)-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 remarkably complex structure that embodies the intricacies of organic chemistry and molecular biology. It consists of multiple stereocenters and functional groups that contribute to its biological activity and interactions.

Key Features

  • Bioactivity: The presence of amino groups signifies potential biological activity, making it interesting for pharmaceutical research, particularly in drug development.
  • Structural Complexity: With multiple ring systems and stereochemistry, this compound presents a challenge for synthetic chemists eager to explore state-of-the-art synthetic techniques.
  • Natural Product Analogue: It may share structural features with naturally occurring substances, which can be pivotal in understanding enzymatic processes or signaling mechanisms in living organisms.
  • Synthetic Challenges: The intricate architecture of this molecule is indicative of the challenges in its synthesis, including controlling stereochemistry during reactions.

Researchers often summarize the significance of such compounds by stating, “The more complex the architecture, the more profound the possibilities for biological activity.” This encapsulates the essence of studying complex molecules like this one, as their sophisticated structures often hold keys to novel therapeutic strategies.

In summary, the exploration of (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R)-5-[(1R,3S,5R,6S)-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 offers a fascinating glimpse into the potential of organic chemistry to innovate and inspire within the scientific community.

Synonyms
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R)-5-[(1R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol
SCHEMBL21293799
UOZODPSAJZTQNH-QGSSWKKLSA-N