2-Amino-2-N-carbobenzoxy-2-deoxy-D-mannose

2-氨基-2-N-苄氧羰基-2-脱氧-D-甘露糖，

N-Carbobenzyloxy Mannosamine (Z-ManNAc) is a synthetic compound that bears close resemblance to sialic acid, which is an essential part of various biological molecules. It is a derivative of Mannose, a monosaccharide sugar, that has been modified to include an additional carbon on its side chain with a phenyl carbamate group on the nitrogen atom. Z-ManNAc is an important intermediate in the biosynthesis of sialic acids and is involved in the post-translational modification of glycoconjugates. It has been used in numerous scientific experiments to study and modulate biological processes related to carbohydrates, proteins, and immune responses.

Synthesis and Characterization:

Z-ManNAc is often synthesized through a multi-step process that involves protecting groups, N-acylation, and deprotection. One commonly used method for Z-ManNAc synthesis is the Fukuyama-type synthesis. This method involves the reaction of Mannose with ethyl 2-aminobenzoate under basic conditions to produce N-benzyloxycarbonyl Mannosamine. This intermediate compound is then reacted with bis(trimethylsilyl) acetamide and trimethylchlorosilane to form the protected Z-ManNAc. The product is then deprotected under acidic conditions to produce pure Z-ManNAc.

The characterization of Z-ManNAc involves various processes, including nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry. These techniques are used to evaluate the purity, identity, and structure of the compound.

Analytical Methods:

Z-ManNAc can be quantified and identified using various analytical methods. HPLC is commonly used to determine the purity and quantity of Z-ManNAc in a sample. This technique employs an aqueous mobile phase and a reversed-phase column to separate the compounds based on size, polarity, and hydrophobicity. Mass spectrometry is another technique used for the detection and identification of Z-ManNAc. It involves ionizing the sample to create charged particles that are separated based on their mass-to-charge ratio. NMR spectroscopy is also used to identify and characterize Z-ManNAc. It is based on the principle that certain nuclei in organic molecules have a magnetic moment and can absorb energy in a magnetic field.

Biological Properties:

Z-ManNAc plays a crucial role in the biosynthesis of sialic acids, which are involved in various biological processes, including cell adhesion, signal transduction, and immune responses. It is also involved in the modulation of T-cell and B-cell activity, inflammation, and cancer cell proliferation. Z-ManNAc has been shown to induce the production of anti-inflammatory cytokines and the activation of regulatory T cells. Furthermore, it has been used in the synthesis of glycans and glycoconjugates, which have widespread applications in biotechnology and structural biology.

Toxicity and Safety in Scientific Experiments:

Z-ManNAc has been extensively tested for its toxicity and safety in scientific experiments. Studies have shown that it has low toxicity in vitro and in vivo. The compound does not induce acute toxicity or genotoxicity, and its LD50 value is relatively high. However, it is recommended to handle Z-ManNAc with caution and follow appropriate safety protocols, especially when working with solvents or other chemicals.

Applications in Scientific Experiments:

Z-ManNAc has numerous applications in scientific research and experimentation. It is often used as a substrate for enzymes involved in the biosynthesis of sialic acids. It is also used in the synthesis of glycoconjugates and glycans, which play crucial roles in various biological processes, including cell-cell interactions, immune responses, and disease progression. Z-ManNAc has been used to study the regulation of immune responses, the modulation of glycan expression, and the function of glycosyltransferases.

Current State of Research:

Research on Z-ManNAc is ongoing, and new applications are being discovered regularly. Recent studies have focused on its potential role in cancer immunotherapies, the development of new therapeutics for autoimmune diseases, and the modulation of immune responses in viral infections. There is also ongoing research on the use of Z-ManNAc in the synthesis of bioactive glycans and glycoconjugates targeting infectious diseases.

Potential Implications in Various Fields of Research and Industry:

Z-ManNAc has potential implications in various fields of research and industry, including biotechnology, drug discovery, and immunotherapy. Its ability to modulate immune responses and the synthesis of glycans and glycoconjugates makes it a valuable tool for developing new therapeutics for various diseases, including cancer and infectious diseases. The compound can also be used in industrial settings, such as the synthesis of bioactive molecules and glycosylated products.

Limitations and Future Directions:

Although Z-ManNAc has numerous applications, it also has its limitations, such as low solubility in water and low bioavailability. Future research directions may focus on improving the synthesis and characterization of Z-ManNAc, exploring its potential in new applications, and developing new delivery systems and formulations to increase its bioavailability and efficacy. Additionally, further research is needed to explore the potential safety concerns and toxicity of Z-ManNAc in more extensive studies.

Conclusion:

N-Carbobenzyloxy Mannosamine (Z-ManNAc) is a versatile compound with numerous applications in scientific research and experimentation. It is involved in the biosynthesis of sialic acids and plays a crucial role in various biological processes, including cell adhesion, immune responses, and disease progression. Z-ManNAc has been extensively studied for its toxicity and safety and has been found to have low toxicity in vitro and in vivo. Its potential implications in various fields of research and industry make it a valuable tool for developing new therapeutics and industrial products.