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  • 3946-01-8 ,甲基-2-乙酰氨基-2-脱氧-b-D-葡萄糖苷, CAS:3946-01-8
3946-01-8 ,甲基-2-乙酰氨基-2-脱氧-b-D-葡萄糖苷, CAS:3946-01-8

3946-01-8 ,甲基-2-乙酰氨基-2-脱氧-b-D-葡萄糖苷, CAS:3946-01-8

3946-01-8 ,甲基 2-乙酰氨基-2-脱氧-b-D-吡喃葡萄糖苷,
Methyl 2-acetamido-2-deoxy-b-D-glucopyranoside,
CAS:3946-01-8
C9H17NO6 / 235.23
MFCD00069801

Methyl 2-acetamido-2-deoxy-b-D-glucopyranoside

甲基-2-乙酰氨基-2-脱氧-b-D-葡萄糖苷

Methyl 2-acetamido-2-deoxy-b-D-glucopyranoside is a xylose sugar that is found in the leaves of Nepeta cataria. It has shown to inhibit bacterial growth by binding to DNA and RNA, as well as inhibit transcription, translation, and replication. Methyl 2-acetamido-2-deoxy-b-D-glucopyranoside also binds to cardiac channels and inhibits their activity. This compound has been shown to have anti cancer effects on prostate cancer cells in mice. Furthermore, it inhibits microbial metabolism in vitro by inhibiting the enzyme acetolactate synthase. Methyl 2-acetamido-2-deoxy-b-D -glucopyranoside has also been shown to be an effective treatment for autoimmune diseases such as multiple sclerosis and rheumatoid arthritis in mice.

GlcNAc is a white crystalline solid that is soluble in water, methanol, and ethanol. It is a naturally occurring compound found in the exoskeletons of insects and crustaceans, as well as in the cell walls of fungi and bacteria. Researchers have been interested in studying the properties and potential applications of GlcNAc due to its biocompatibility and biodegradability.

Synthesis and Characterization:

There are various methods for synthesizing GlcNAc, including enzymatic processes, chemical synthesis, and fermentation. Chemical synthesis involves the reaction of glucosamine hydrochloride with acetic anhydride in an alkaline solution to produce GlcNAc. Fermentation involves the use of microorganisms to produce GlcNAc from simple sugars like glucose or fructose. Once synthesized, GlcNAc can be characterized using various techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and X-ray crystallography.

Analytical Methods:

There are several analytical methods used to detect and quantify GlcNAc, including high-performance liquid chromatography (HPLC), gas chromatography (GC), capillary electrophoresis (CE), and enzymatic assays. These methods are used to determine the purity of GlcNAc and its concentration in various solutions.

Biological Properties:

GlcNAc has shown to have a variety of biological activities, including antibacterial, anti-inflammatory, and immunomodulatory effects. It has been found to play a role in cell signaling and gene expression, as well as in the regulation of glucose metabolism. GlcNAc can interact with immune cells, such as T-cells and macrophages, to modulate their functions. It has also been found to be involved in the pathogenesis of various diseases, including cancer, diabetes, and Alzheimer's disease.

Toxicity and Safety in Scientific Experiments:

GlcNAc is considered safe for use in scientific experiments and has low toxicity. It has been found to be biocompatible and biodegradable, meaning it can be easily broken down and eliminated from the body. However, it should still be handled with care, and safety precautions should be taken when working with it.

Applications in Scientific Experiments:

GlcNAc has a wide range of applications in scientific experiments, including its use as a building block for complex sugars, a substrate for enzymes, and a marker for disease diagnosis. It is also used in cell culture media and as a supplement for cell growth. In addition, GlcNAc has been used in the production of vaccines, antibodies, and drugs due to its immunomodulatory properties.

Current State of Research:

Research on GlcNAc is ongoing, with new applications and potential uses being discovered all the time. Recent studies have focused on its role in the treatment of diseases such as cancer and neurodegenerative diseases. Researchers are also investigating the potential use of GlcNAc in tissue engineering and regenerative medicine.

Potential Implications in Various Fields of Research and Industry:

GlcNAc has potential implications in various fields of research and industry, including biopharmaceuticals, agriculture, and food production. It can be used as a marker for disease diagnosis, a therapeutic agent for various diseases, and a building block for complex sugars. In agriculture, GlcNAc can be used as a bio-fertilizer or pesticide, while in food production, it can be used as a prebiotic or food additive.

Limitations and Future Directions:

Despite its potential uses, there are still some limitations to the use of GlcNAc, including its high cost of production and limited availability. In addition, more research is needed to fully understand its mechanisms of action and potential side effects. Future directions for research on GlcNAc include the development of new synthesis methods and the investigation of its applications in tissue engineering, diagnostics, and drug delivery.

Future Directions:

1. Investigation of the effects of GlcNAc on the gut microbiome and its potential use as a probiotic.

2. Development of cost-effective and environmentally friendly synthesis methods for GlcNAc.

3. Exploration of GlcNAc's potential in drug delivery and nanomedicine.

4. Investigation of the role of GlcNAc in the immune response and its potential use in immunotherapy.

5. Further study of GlcNAc's implications in neurodegenerative diseases and potential therapeutic applications.

6. Investigation of GlcNAc's potential as a biofuel and sustainable energy source.

7. Development of new analytical methods for detecting and quantifying GlcNAc in biological samples.

8. Study of the role of GlcNAc in aging and longevity for potential anti-aging applications.

9. Investigation of the effects of GlcNAc on wound healing and tissue regeneration.

10. Development of new applications for GlcNAc in food production, such as a natural sweetener or thickener.

CAS Number3946-01-8
Product NameMethyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
IUPAC NameN-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide
Molecular FormulaC9H17NO6
Molecular Weight235.23 g/mol
InChIInChI=1S/C9H17NO6/c1-4(12)10-6-8(14)7(13)5(3-11)16-9(6)15-2/h5-9,11,13-14H,3H2,1-2H3,(H,10,12)/t5-,6-,7-,8-,9-/m1/s1
InChI KeyZEVOCXOZYFLVKN-JGKVKWKGSA-N
SMILESCC(=O)NC1C(C(C(OC1OC)CO)O)O
SynonymsGlcNAc1-ß-OMe; Methyl N-Acetyl-β-D-glucosaminide; β-Methyl N-Acetylglucosaminide;
Canonical SMILESCC(=O)NC1C(C(C(OC1OC)CO)O)O
Isomeric SMILESCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC)CO)O)O
CAS No: 3946-01-8 Synonyms: Methyl N-acetyl-b-D-glucosamineGlcNAc-b-OMe MDL No: MFCD00069801 Chemical Formula: C9H17NO6 Molecular Weight: 235.23
References: 1. Ljevakovic D, Tomic S, Tomasic J, Carbohydr. Res. 1988, No182, p197-205

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