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Streptomycin

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Identification
Molecular formula
C21H39N7O12
CAS number
57-92-1
IUPAC name
2-[(1R,2R,3S,5R,6S)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]oxy-3-guanidino-2,5,6-trihydroxy-cyclohexyl]guanidine
State
State

Streptomycin is solid at room temperature. It is usually found in a powdered form for medical and laboratory use, and it is highly soluble in water.

Melting point (Celsius)
122.00
Melting point (Kelvin)
395.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
581.57g/mol
Molar mass
581.5730g/mol
Density
1.4400g/cm3
Appearence

Streptomycin typically appears as a white or almost white crystalline powder. It is generally odourless but may have a faint characteristic odour. The compound is often available as a sulfate salt for use in medical formulations.

Comment on solubility

Solubility of 2-[(1R,2R,3S,5R,6S)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]oxy-3-guanidino-2,5,6-trihydroxy-cyclohexyl]guanidine

The solubility of complex organic compounds such as 2-[(1R,2R,3S,5R,6S)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]oxy-3-guanidino-2,5,6-trihydroxy-cyclohexyl]guanidine is influenced by several factors:

  • Hydroxyl Groups: The presence of multiple hydroxyl (–OH) groups suggests the potential for strong hydrogen bonding with solvents, which typically enhances solubility in polar solvents, particularly water.
  • Molecular Complexity: With its intricate structure and stereochemistry, solubility can vary significantly depending on the specific orientation of these functional groups and the resulting steric hindrance.
  • Polarity: As a highly polar molecule due to its numerous functional groups, it is likely to be more soluble in polar solvents than in nonpolar ones.

It can be said that "the more hydroxyl groups, the better the solubility in water," but the overall solubility behavior must be confirmed through empirical methods as real-world interactions can sometimes defy theoretical predictions.

Given these factors, it is essential to conduct solubility testing in various solvents to elucidate the most suitable conditions for this compound's dissolution.

Interesting facts

Interesting Facts about 2-[(1R,2R,3S,5R,6S)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]oxy-3-guanidino-2,5,6-trihydroxy-cyclohexyl]guanidine

This compound is a fascinating example of a complex organic molecule, exhibiting multiple functional groups and stereocenters. Here are some compelling aspects to consider:

  • Stereochemistry: The compound contains several stereocenters, which contributes to its three-dimensional shape and can significantly affect its reactivity and interaction with biological systems.
  • Biological Relevance: Many compounds with similar structures are evaluated for their potential therapeutic effects, such as in the treatment of diseases like diabetes or obesity due to their ability to mimic or inhibit biological pathways.
  • Functional Groups: The presence of guanidine and multiple hydroxyl groups suggests potential for hydrogen bonding in biological systems, which may contribute to the compound's solubility and interactions with enzymes or receptors.
  • Natural vs. Synthetic: Understanding whether compounds like this are derived from natural sources or synthesized in laboratories reveals important insights into medicinal chemistry and drug design.
  • Structure-Activity Relationship (SAR): Studying this compound opens up avenues for exploring how structural changes influence biological activity, leading to the design of more effective derivatives.

In summary, this intricate molecule encapsulates the beauty of organic chemistry, where small changes can result in significant shifts in functionality. The exploration of such compounds underlines the importance of stereochemistry, functional group interactions, and the ongoing efforts in drug discovery.