N-Acetyl-D-glucosamine

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Identification

Molecular formula
C8H15NO6
CAS Number
7512-17-6
IUPAC Name
N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
Molecular Weight
221.21g/mol
Melting Point
(Celsius)
Boiling Point
(Celsius)
Density
1.6350g/cm3
Synonyms
N-Acetyl-beta-D-glucosamine
Interesting facts

Interesting Facts About N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide

This compound is a fascinating example of a modified sugar derivative that showcases the complexities of carbohydrate chemistry. Often referred to in research as a glycosylated amide, it possesses remarkable structural features that can lead to unique biological activities.

Structural Significance

  • Chirality: The presence of multiple chiral centers (2R, 3R, 4R, 5S, 6R) adds to its stereogenic nature, impacting its interactions with biological systems.
  • Hydroxyl Groups: With three hydroxyl groups, this compound is expected to exhibit strong hydrogen bonding capabilities, affecting its solubility and reactivity.
  • Hydroxymethyl Group: The hydroxymethyl modification could enhance its stability and potentially influence its role in enzymatic reactions.

Biological Relevance

This compound is of great interest in pharmaceutical research due to its potential therapeutic applications. Here are some key points:

  • Drug Design: Its glycosidic structure could serve as a lead compound in the design of new drugs, particularly in treating diseases where carbohydrate interactions play a key role, such as viral infections.
  • Metabolic Pathways: Compounds like this can mimic natural substrates in various metabolic pathways, making them valuable in the study of metabolism and enzyme kinetics.

Research Implications

Researchers are increasingly focused on understanding how such molecules can influence metabolic processes. Its examination may lead to:

  • Insights into enzyme inhibition or activation mechanisms.
  • Development of selective inhibitors or modulators for various biological pathways.
  • Application in creating targeted delivery systems in drug formulation.

In summary, N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide stands out not only for its complex structure but also for its potential applications in modern chemistry and medicine. Its exploration opens up new avenues for research and innovation in the fields of biochemistry and pharmacology.

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