Phenyl 2-acetamido-2-deoxy-b-D-glucopyranoside

苯基-2-乙酰氨基-2-脱氧-beta-D-葡萄糖苷

Phenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside (PAG) is a chemical compound derived from N-acetylglucosamine that is widely used as a substrate in different enzymatic assays, in lectin affinity chromatography, and as a chiral selector for capillary electrophoresis. This paper aims to provide a comprehensive overview of the properties, synthesis, characterization, analytical methods, biological activities, safety, and potential applications of PAG, as well as its current state of research, limitations, and future directions.

Definition and Background:

Phenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside (PAG) is a glycan with a phenyl group attached to the C2 position of the N-acetylglucosamine (GlcNAc) moiety. It has the chemical formula C14H19NO7 and a molecular weight of 317.3 g/mol (Jenkins et al., 2010). PAG is a white crystalline powder that is soluble in water, methanol, and ethanol but insoluble in nonpolar solvents. It is a non-toxic, non-carcinogenic, and non-corrosive compound that is stable at room temperature and acidic pH (Liu et al., 2018).

Physical and Chemical Properties:

PAG has several physical and chemical properties that make it useful for different applications. It has a melting point of 195-197°C and a specific rotation of +20.7° (c=1, H2O). PAG has a high affinity for various lectins, including wheat germ agglutinin (WGA), concanavalin A (ConA), and soybean agglutinin (SBA), due to the presence of a GlcNAc residue in its structure (Jenkins et al., 2010). PAG can also be fluorescently labeled with different dyes, such as 2-aminobenzamide (2-AB) and 2-aminobenzoic acid (2-AA), to enhance its detection and visualization by different analytical techniques (Liu et al., 2018).

Synthesis and Characterization:

The synthesis of PAG can be achieved by several methods, including the reaction of phenyl isocyanate with GlcNAc in the presence of anhydrous potassium carbonate, or the reaction of phenyllithium with 2-azido-2-deoxy-D-glucopyranose in the presence of boron trifluoride etherate (Jenkins et al., 2010). The characterization of PAG can be done by different techniques, including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE) (Liu et al., 2018).

Analytical Methods:

PAG can be analyzed by different analytical methods, depending on its intended application. For lectin affinity chromatography, PAG can be immobilized on a solid support, such as agarose or Sepharose, and used to purify and separate lectins from biological samples (Jenkins et al., 2010). For enzymatic assays, PAG can be used as a substrate to test the activity of different enzymes, such as beta-galactosidase or beta-N-acetylglucosaminidase, that hydrolyze the glycosidic bond between the GlcNAc and the phenyl group (Liu et al., 2018).

Biological Properties:

PAG has been shown to have several biological properties that make it interesting for biomedical research. It can inhibit the adhesion of pathogenic bacteria, such as Escherichia coli and Staphylococcus aureus, to host cells by blocking their interactions with specific lectins (Wagner et al., 2013). PAG can also act as a chiral selector for capillary electrophoresis, allowing the separation and analysis of different enantiomers of drug molecules (Matsuda et al., 2011). Furthermore, PAG has been used as a tool to study the glycosylation patterns of proteins in different biological systems, such as cancer cells and immune cells, by labeling their glycans with PAG and analyzing them by CE or MS (Dekker et al., 2018).

Toxicity and Safety in Scientific Experiments:

PAG has been shown to be non-toxic, non-carcinogenic, and non-corrosive, and it does not pose any significant risk to human health or the environment when handled according to standard laboratory practices. However, like any chemical compound, PAG should be handled with care and disposed of properly, following the local regulations and guidelines for chemical waste management.

Applications in Scientific Experiments:

PAG has several applications in scientific experiments, including lectin affinity chromatography, enzymatic assays, and chiral separations. It can also be used as a fluorescent tag for the detection and analysis of glycans in different biological systems, such as glycoproteins, glycolipids, and bacteria. Furthermore, PAG can be used to study the interactions between lectins and their ligands, such as sulfated glycans, heparan sulfates, or sialylated glycans, by competing with them for binding to the lectin (Wagner et al., 2013).

Current State of Research:

The research on PAG has mainly focused on its applications in glycan analysis, lectin-based assays, and biomedical research. Recent studies have shown the potential of PAG as a tool to investigate the glycosylation of cancer cells and to develop glycan-based therapies and diagnostics for cancer (Dekker et al., 2018). Furthermore, PAG has been used to study the interactions between viruses and host cells, as well as the role of glycans in viral entry and infection (Wang et al., 2020).

Potential Implications in Various Fields of Research and Industry:

The potential implications of PAG in various fields of research and industry are numerous. PAG can be used in the development of new lectin-based diagnostic tests and therapies for infectious diseases, cancer, and autoimmune disorders. It can also be used to improve the efficiency and specificity of enzymatic assays and to facilitate the discovery of new enzyme inhibitors and activators. Furthermore, PAG can be used to study the role of glycans in different biological systems, such as gene expression, protein folding, and cell signaling (Liu et al., 2018).

Limitations and Future Directions:

Despite its many applications and advantages, PAG has some limitations that need to be addressed in future research. One limitation is the high cost and complexity of its synthesis, which limits its availability and scalability. Another limitation is the lack of standardization and harmonization of the analytical methods used to measure PAG and other glycans, which hinders their comparability and reproducibility. Future research on PAG and other glycans should focus on developing more efficient and cost-effective synthesis methods, improving the analytical methods for glycan detection and quantification, and exploring the biological roles and functions of specific glycans in health and disease. Some future directions for research on PAG are:

- Developing new PAG derivatives with different chemical and biological properties, such as increased affinity for lectins or enhanced fluorescent properties.

- Investigating the role of PAG and other glycans in the regulation of immune responses and inflammation, and the potential of glycan-based therapies for autoimmune disorders and chronic diseases.

- Studying the structural and functional diversity of glycans in different biological systems, such as bacteria, fungi, and plants, and their potential as sources of new bioactive compounds and materials.

- Developing new analytical methods for glycan imaging and mapping in complex biological systems, such as tissues and organs, and their applications in disease diagnosis and treatment.