Benzyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-b-D-glucopyranoside

苄基-2-乙酰氨基-2-脱氧-3,4,6-O-三乙酰基-b-D-葡萄糖苷

Benzyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-b-D-glucopyranoside is a synthetic sugar that is used as a glycosylation reagent for the synthesis of oligosaccharides and polysaccharides. It reacts with saccharides in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). The benzyl group can be modified to include fluorine atoms or methyl groups. This compound is an important building block for the synthesis of complex carbohydrates.

Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside, also known as Benzyl N-acetyl-beta-D-glucosaminide (Bn-GlcNAc) or 3,4,6-tri-O-acetyl-2-(benzyloxycarbonylamino)-2-deoxy-D-glucopyranosyl acetate, is a synthetic carbohydrate derivative. It is a type of N-acetylglucosaminide, which is commonly found in the human body as a component of chitin, a major structural component of the exoskeletons of arthropods such as insects and crustaceans.

Physical and Chemical Properties:

Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside is a white to off-white crystalline powder, stable at room temperature. It is soluble in most organic solvents but insoluble in water. 

Synthesis and Characterization:

Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside can be synthesized through several methods, including chemical synthesis and enzymatic synthesis. The chemical synthesis involves the reaction of N-acetylglucosamine with benzyl chloroformate, while the enzymatic synthesis involves the use of glucosamine-6-phosphate and acetyl coenzyme A as substrates for the enzyme N-acetylglucosamine-2-epimerase. The synthesized product can be characterized using the techniques of nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and infrared spectroscopy.

Analytical Methods:

Various analytical methods are used to determine the purity and identity of Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside such as thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE). These methods are used to ensure the quality and consistency of the synthesized product in scientific experiments.

Biological Properties:

Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside has been found to exhibit biological activities such as inhibition of bacterial growth and virulence. It also acts as a substrate for enzymes such as N-acetylglucosaminidases, which play a role in various biological processes such as cell signaling and the immune response.

Toxicity and Safety in Scientific Experiments:

Studies have shown that Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside is non-toxic at low concentrations and has a low risk of side effects in scientific experiments. However, due to its synthetic nature, it is important to follow safety protocols and use caution when handling this compound.

Applications in Scientific Experiments:

Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside has a wide range of applications in scientific experiments. It is used as a substrate for enzymes and in the synthesis of glycopeptides and glycoproteins. It is also used in the study of various biological processes such as protein folding and glycosylation.

Current State of Research:

Research on Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside is ongoing, with new applications and potential uses being discovered. Studies continue to explore its biological activities and potential as a therapeutic agent.

Potential Implications in Various Fields of Research and Industry:

Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside has potential implications in various fields of research and industry such as drug development, biotechnology, and materials science. Its ability to inhibit bacterial growth and virulence makes it a potential candidate for the development of new antibiotics. Its use as a substrate in the synthesis of glycopeptides and glycoproteins has implications for the development of new drugs and therapeutics. Additionally, its use in materials science for the development of new organic materials and polymers is also being explored.

Limitations and Future Directions:

One limitation of Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside is its low solubility in water, which limits its use in aqueous environments. Another limitation is its synthetic nature, which may limit its potential use in biological systems. Future research could focus on developing new methods for synthesizing this compound and exploring its potential use in various fields. Possible future directions include exploring its use in drug delivery systems, its potential as a therapeutic agent for various diseases, and its use in materials science for the development of new materials and polymers.