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Zidovudine

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Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate
State
State

At room temperature, zidovudine is in a solid state. It is commonly utilized in tablet or capsule forms as an antiretroviral medication for HIV treatment.

Melting point (Celsius)
123.00
Melting point (Kelvin)
396.15
Boiling point (Celsius)
596.90
Boiling point (Kelvin)
870.10
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
1.6100g/cm3
Appearence

Zidovudine typically appears as a white to off-white crystalline powder. It is usually in a solid form and distinct in its crystalline nature, often employed in its solid-state for pharmaceutical formulations.

Comment on solubility

Solubility of [(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate

The solubility of this complex compound is influenced by several factors, particularly its functional groups and overall molecular structure. Here are some key points to consider:

  • Polar Functionality: The presence of hydroxyl (–OH) and acetamido (–NHCOCH3) groups typically enhances solubility in polar solvents, especially water.
  • Hydrophilicity vs. Hydrophobicity: While the multiple hydroxyl groups generally promote solubility, the hydrophobic regions of the molecule may hinder it slightly depending on the overall balance.
  • Salt Formation: The hydrogen phosphate moiety can interact with water to form a salt, contributing positively to solubility.
  • Concentration Effects: Solubility can vary significantly with concentration; higher concentrations may lead to saturation, limiting further dissolution.

As a whole, one could anticipate that this compound exhibits modest to good solubility in polar solvents like water due to its functional groups. However, the intricate balance between hydrophilic and hydrophobic aspects means that testing in specific conditions is crucial to ascertain its precise solubility profile.

Interesting facts

Interesting Facts about [ (2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] [[ (2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate

This fascinating compound is a complex derivative of carbohydrates and nucleic acid-related structures, showcasing the intricate interplay between sugars and phosphates in biological systems. Here are some notable points about this compound:

  • Biochemical Significance: This compound can be viewed as a hybrid of saccharides and nucleotide components, hinting at its potential roles in metabolism or cell signaling.
  • Stereochemistry: The precise arrangement of its stereocenters (as indicated by the stereochemical descriptors) is crucial, as even subtle changes in stereochemistry can significantly affect biological activity.
  • Functional Groups: The presence of functional groups like acetamido and phosphoryl points to its possible involvement in phosphoryl transfer reactions, which are vital for energy transfer and signal transduction within cells.
  • Research Application: Compounds of this nature are often central to studies in medicinal chemistry and drug design, particularly in targeting specific enzymatic pathways or mimicking natural substrates.
  • Structural Diversity: The combination of the tetrahydropyran and tetrahydrofuran rings exemplifies the structural diversity often found in carbohydrate derivatives, which can lead to novel interactions with proteins or other biomolecules.
  • Quote from a Chemist: "Understanding the complex behavior of such compounds can lead not only to enhanced drug design but also a deeper appreciation of life's molecular machinery."

This compound stands as a testament to the complexity of biological molecules and their rich chemistry, providing endless avenues for exploration in both fundamental and applied research.

Synonyms
Udpgnac
Udp acetylglucosamine
Uridine diphosphate-N-acetylglucosamine
Uridine pyrophosphoacetylglucosamine
uridine diphosphate N-acetylglucosamine
528-04-1
Uridine diphospho-N-acetylglucosamine
[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
Acetylglucosamine, UDP
Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-alpha-D-glucopyranosyl) ester
bmse000188
DTXSID10912327
[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate