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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
State
State

At room temperature, N-Acetyl-D-glucosamine exists as a solid.

Melting point (Celsius)
221.00
Melting point (Kelvin)
494.15
Boiling point (Celsius)
481.00
Boiling point (Kelvin)
754.15
General information
Molecular weight
221.21g/mol
Molar mass
221.2080g/mol
Density
1.6350g/cm3
Appearence

The compound typically appears as a white crystalline powder. It is odorless and is known for its sweetness, being less sweet than sucrose.

Comment on solubility

Solubility of N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide

The solubility characteristics of N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide can be discussed in several key aspects:

  • Polar Nature: This compound contains multiple hydroxyl (-OH) groups, which are polar functional groups that significantly enhance its solubility in polar solvents, particularly water.
  • Hydrogen Bonding: The presence of hydroxyl groups allows for extensive hydrogen bonding with water molecules. This interaction is crucial for its high solubility in aqueous solutions.
  • Solvent Compatibility: Beyond water, this compound may also exhibit solubility in other polar solvents like methanol and ethanol, though solubility may decrease in nonpolar organic solvents due to the lack of favorable interactions.
  • Concentration Considerations: The actual solubility can depend on various factors, including temperature, pH, and the specific solvent used, meaning solubility might vary under different conditions.

In summary, while N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide is expected to have good solubility in polar solvents due to its hydroxyl groups that facilitate strong hydrogen bonding, practical applications and specific solubility levels may vary based on external conditions and solvent choice. This underscores the importance of considering these factors during laboratory preparations and reactions.

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.

Synonyms
N-Acetyl-beta-D-glucosamine
2-acetamido-2-deoxy-beta-D-glucopyranose
betaGlcNAc
GlcNAc-beta
CHEBI:28009
beta-N-Acetylglucosamin
2-Acetamido-2-deoxy-beta-D-glucose
2-acetamido-2-deoxyhexopyranose
8P59336F68
UNII-8P59336F68
Glucopyranose, 2-acetamido-2-deoxy-, beta-D-
WURCS=2.0/1,1,0/(a2122h-1b_1-5_2*NCC/3=O)/1/
acetylglucosamine
Beta-N-Acetylglucosamine
14131-68-1
2-Acetamido-2-deoxy-beta-D-glucosamine
N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
N-Acetyl Glucosamine
103094-10-6
137630-09-2
1398-61-4
72-87-7
NAcGlc
Cheon shim bo yun
n-acetyl-b-d-glucosamine
C8H15NO6
pharmaceutical aid
ssGlcNAc-R
Crab Shell Chitin
b-N-Acetylglucosamine
Spectrum_000999
Spectrum2_001353
Spectrum3_001400
Spectrum4_001179
b-N-Acetyl-D-glucosamine
bmse000231
Epitope ID:135813
beta-N-Acetyl-D-glucosamine
SCHEMBL19345
BSPBio_003020
KBioGR_001817
KBioSS_001479
DivK1c_000352
SPECTRUM1500715
n-acetyl-.beta.-d-glucosamine
SPBio_001565
CHEMBL447878
beta-N-Acetyl-delta-glucosamine
CHEBI:17029
HMS501B14
KBio1_000352
KBio2_001479
KBio2_004047
KBio2_006615
KBio3_002240
.BETA.-N-ACETYLGLUCOSAMIN
[4)-beta-D-GlcpNAc(1->]n
2-Acetamido-2-deoxy-b-D-glucose
NINDS_000352
DTXSID301045979
HMS1921E22
N-Acetyl-D-glucosamine, USP grade
BDBM50481442
CCG-39291
AKOS015960418
AT21015
2-Acetamido-2-deoxy-beta-delta-glucose
IDI1_000352
N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
NCGC00178341-01
[1,4-(N-Acetyl-beta-D-glucosaminyl)]n
2-deoxy-2-acetamido-beta-D-glucopyranose
AC-11093
(1->4)-2-acetamido-2-deoxy-beta-D-glucan
2-(acetylamino)-2-deoxy-beta-D-glucopyranose
2-ACETAMIDO-2-DEOXY-.BETA.-D-GLUCOSE
C03878
N-acetyl-D-glucosamine (complete stereochemistry)
Q284367
2-ACETAMIDO-2-DEOXY-.BETA.-D-GLUCOPYRANOSE
GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-, .BETA.-D-
Poly-(b1-4)-N-acetyl glucosamine/Poly-(a1-4)-N-acetyl glucosamine