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  • 7784-54-5 ,  alpha-D-氨基葡萄糖五乙酸酯, CAS:7784-54-5
7784-54-5 ,  alpha-D-氨基葡萄糖五乙酸酯, CAS:7784-54-5

7784-54-5 , alpha-D-氨基葡萄糖五乙酸酯, CAS:7784-54-5

7784-54-5 , 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose,
alpha-D-氨基葡萄糖五乙酸酯,
CAS:7784-54-5
C16H23NO10 / 389.355
MFCD00065051

2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-a-D-glucopyranose

alpha-D-氨基葡萄糖五乙酸酯,

2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-a-D-glucopyranose (2AAT) is a synthetic nucleoside that binds to the same sequence of n-acetylgalactosamine in the cell wall of Gram positive bacteria. It was found to be effective against bacterial strains that produce beta lactamase enzymes. 2AAT has been shown to inhibit the growth of Gram positive bacteria and is able to penetrate tissues. It also prevents bacterial DNA gyrase and topoisomerase IV from binding with their respective substrates. 2AAT is made up of four parts: two ribose molecules, one deoxyribose molecule and one acetamido group. This last part is what makes it bind to the bacterial cell wall and inhibits protein synthesis by preventing mRNA from being translated into proteins.

Alpha-D-glucosamine pentaacetate is a chemical compound that has garnered much attention in the scientific community due to its various beneficial properties and potential implications in different fields of research and industry. In this paper, we will explore in detail the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions of alpha-D-glucosamine pentaacetate.

Physical and Chemical Properties:

The physical and chemical properties of alpha-D-glucosamine pentaacetate make it a unique molecule with diverse applications in different fields of research and industry. It has a high degree of purity, stability, and solubility, making it an ideal candidate for chemical and biochemical studies. Alpha-D-glucosamine pentaacetate is also biodegradable and non-toxic, making it safe for use in various applications.

Synthesis and Characterization:

Alpha-D-glucosamine pentaacetate can be synthesized from chitin through a series of chemical reactions. The synthesis involves the deacetylation of chitin to produce chitosan, which is then acetylated to produce alpha-D-glucosamine pentaacetate. The purity, structure, and composition of alpha-D-glucosamine pentaacetate can be characterized using various analytical techniques, including nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry.

Analytical Methods:

Analytical methods are essential tools for studying alpha-D-glucosamine pentaacetate, as they provide information on its purity, composition, and structure. Different analytical methods, including chromatography, spectrophotometry, and electrophoresis, can be used to analyze alpha-D-glucosamine pentaacetate.

Biological Properties:

Alpha-D-glucosamine pentaacetate has several biological properties that make it an interesting molecule for biomedical and pharmaceutical research. It has anti-inflammatory, anti-tumor, and immunomodulatory properties, making it a potential candidate for developing drugs for different diseases.

Toxicity and Safety in Scientific Experiments:

The safety and toxicity of alpha-D-glucosamine pentaacetate have been studied extensively in vitro and in vivo experiments. It has been shown to be non-toxic even at high doses and has no adverse effects on human health.

Applications in Scientific Experiments:

Alpha-D-glucosamine pentaacetate has several applications in scientific experiments, including drug delivery, wound healing, tissue engineering, and gene therapy. It can also be used to develop diagnostic tools for different diseases.

Current State of Research:

There is ongoing research on the different applications of alpha-D-glucosamine pentaacetate, including its use as a drug delivery agent, anti-inflammatory agent, immune-modulator, tissue engineering, and wound healing. Researchers are also exploring the potential of alpha-D-glucosamine pentaacetate in developing new diagnostic tools and therapies for various diseases.

Potential Implications in Various Fields of Research and Industry:

Alpha-D-glucosamine pentaacetate has potential implications in various fields of research and industry, including pharmaceuticals, biomedical research, and agriculture. It can be used to develop new drugs for different diseases, gene therapy, wound healing, skin care, and cosmetics.

Limitations and Future Directions:

Despite its many beneficial properties, alpha-D-glucosamine pentaacetate has some limitations that need to be addressed in future research. These include its limited solubility in water, poor oral bioavailability, and potential instability in some environments. Future research should focus on developing new synthesis methods, improving its solubility, developing new delivery systems, and increasing its stability.

Future Directions:

There are several future directions for research on alpha-D-glucosamine pentaacetate. These include improving its solubility and stability, developing new delivery systems, exploring its potential as a drug-targeting agent, and investigating its use in agriculture. Researchers can also study the interactions between alpha-D-glucosamine pentaacetate and various biological molecules to elucidate its mechanisms of action.

CAS Number7784-54-5
Product Namealpha-D-Glucosamine pentaacetate
IUPAC Name[(2R,3S,4R,5R)-5-acetamido-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
Molecular FormulaC16H23NO10
Molecular Weight389.355 g/mol
InChIInChI=1S/C16H23NO10/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16?/m1/s1
InChI KeyOVPIZHVSWNOZMN-QCODTGAPSA-N
SMILESCC(=O)NC1C(C(C(OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
Synonyms2-(Acetylamino)-2-deoxy-α-D-glucopyranose 1,3,4,6-Tetraacetate; 1,3,4,6-Tetra-O-acetyl-2-acetamido-2-deoxy-α-D-glucopyranose; N-Acetyl-α-D-glucosamine Tetraacetate; NSC 231931;
Canonical SMILESCC(=O)NC1C(C(C(OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C


CAS No: 7784-54-5 Synonyms: 1,2,3,4,6-Penta-O-acetyl-a-D-glucosaminea-D-Glucosamine pentaacetate2-(Acetylamino)-2-deoxy-a-D-glucopyranose

 1,3,4,6-tetraacetate MDL No: MFCD00065051 Chemical Formula: C16H23NO10 Molecular Weight: 389.355

COA:

Product name: 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose; alpha-D-Glucosamine pentaacetate

CAS: 7784-54-5         M.F.: C16H23NO10         M.W.: 389.355         Batch No: 20131228       Quantity:40g from 246g

Items

Standards

Results

Appearance

White crystalline powder

Positive

Solubility

Soluble in DMF, insoluble in water

Complies

Identification

IR and HPLC

Positive

MS and NMR

Should Comply

Complies

Assay by HPLC

Min. 97%

99.2%

References:

1. Bernacki RJ, Sharma M, Porter NK, Rustum Y, Paul B, Korytnyk W, Journal of Supramolecular Structure, 2004, 7, 2, p235-250
2. Cudic, P., et al., Bioorg. Med. Chem. Lett., 11, 3107 (2001)

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