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577-76-4,Chitobiose 2HCl,CAS:577-76-4

577-76-4,Chitobiose 2HCl,CAS:577-76-4
C12H24N2O9•2HCl
MFCD06801377

Chitobiose 2HCl壳二糖二盐酸盐 ,Chitobiose 2HCl

Beta-D-glucosaminyl-(1->4)-aldehydo-D-glucosamine (GlcNAc) is a common monosaccharide and a critical building block of complex carbohydrates such as glycoproteins and glycolipids. GlcNAc is an essential component of structural proteins, extracellular matrices, and cell membranes, and serves as a key regulator of biological processes such as cell-cell interactions, signaling pathways, and immune responses. This paper provides a comprehensive overview of the physical and chemical properties, synthesis and characterization, analytical methods, biological properties, and potential implications of GlcNAc in various fields of research and industry.

Background and Definition

GlcNAc is a derivative of glucose with an amide group attached to the C2 position of the sugar moiety, which distinguishes it from other monosaccharides. GlcNAc is a white crystalline powder with a sweet taste and a molecular weight of 221.21 g/mol. GlcNAc is a naturally occurring sugar found in various sources such as shellfish, mushrooms, and chitin, which is a polymer of GlcNAc found in the exoskeleton of arthropods and fungi.

Physical and Chemical Properties

GlcNAc exhibits various physical and chemical properties that are essential for its biological functions. GlcNAc is a polar molecule with a high melting point (212-213°C) and a moderate solubility in water (60 g/L). GlcNAc can be easily modified to form glycosaminoglycans, which are long chains of repeating sugar units that are important for the structural integrity of connective tissues.

Synthesis and Characterization

GlcNAc can be synthesized from glucose using various chemical and enzymatic methods. Chemical synthesis involves the conversion of glucose into glucosamine, which is then acylated with acetyl chloride to form GlcNAc. Enzymatic synthesis involves the use of N-acetylglucosaminyltransferases to transfer N-acetylglucosamine residues from UDP-GlcNAc to the acceptor substrates. GlcNAc can be characterized by various analytical techniques such as nuclear magnetic resonance spectroscopy, X-ray crystallography, and mass spectrometry.

Analytical Methods

GlcNAc can be analyzed by various analytical methods depending on the application and the required sensitivity and accuracy. High-performance liquid chromatography (HPLC) is a common method used to separate and quantify GlcNAc and its derivatives in biological samples. Capillary electrophoresis (CE) is another method used to analyze GlcNAc and its derivatives based on their charge-to-mass ratios. Mass spectrometry (MS) is a powerful analytical method used to identify and quantify GlcNAc and its derivatives based on their molecular masses and fragmentation patterns.

Biological Properties

GlcNAc exhibits various biological properties that are critical for its role in cellular and molecular processes. GlcNAc plays a crucial role in protein glycosylation, which is a post-translational modification that involves the attachment of sugar residues to proteins. Glycosylation is essential for the folding, stability, and function of proteins, and is involved in various biological processes such as cell signaling, immune responses, and cell adhesion. GlcNAc is also involved in the synthesis of chitin, which is an important structural molecule found in various organisms such as insects, crustaceans, and fungi.

Toxicity and Safety in Scientific Experiments

GlcNAc has been shown to be safe and non-toxic in scientific experiments at physiological concentrations. However, high doses of GlcNAc may have adverse effects such as gastrointestinal discomfort, allergic reactions, and insulin resistance. Therefore, caution should be exercised when using GlcNAc at high doses in scientific experiments.

Applications in Scientific Experiments

GlcNAc has various applications in scientific experiments, particularly in the fields of glycobiology, biochemistry, and immunology. GlcNAc is used as a substrate for glycosyltransferases and as a building block for the synthesis of glycans and glycoconjugates. GlcNAc is also used as a tool for studying protein glycosylation, cell signaling, and immune responses. GlcNAc has potential applications in drug discovery, diagnostics, and biotechnology.

Current State of Research

The research on GlcNAc has been rapidly expanding in recent years, particularly in the areas of protein glycosylation, immune responses, and metabolic disorders. The development of advanced analytical methods and tools has facilitated the discovery and characterization of new roles and functions of GlcNAc in various biological processes.

Potential Implications in Various Fields of Research and Industry

GlcNAc has potential implications in various fields of research and industry, particularly in the areas of drug discovery, diagnostics, and biotechnology. GlcNAc-based drugs and therapeutics may have potential applications in the treatment of various diseases such as cancer, inflammation, and metabolic disorders. GlcNAc-based diagnostics may have potential applications in the early detection and diagnosis of various diseases. GlcNAc-based biotechnology may have potential applications in the production of high-value glycoconjugates and immunogens.

Limitations and Future Directions

Despite the significant advances in research on GlcNAc, several limitations and challenges still need to be addressed. One of the limitations is the limited availability of high-quality GlcNAc-based reagents and tools. Another limitation is the diversity and complexity of protein glycosylation, which makes it challenging to study and manipulate. Future directions in research on GlcNAc include the development of new analytical methods and tools, the identification of new roles and functions of GlcNAc in various biological processes, and the development of new GlcNAc-based drugs, diagnostics, and biotechnology products.

Conclusion

In conclusion, GlcNAc is a critical building block of complex carbohydrates and plays essential roles in various biological processes such as protein glycosylation, immune responses, and chitin synthesis. GlcNAc has various physical and chemical properties, and can be synthesized using various chemical and enzymatic methods. GlcNAc can be analyzed by various analytical methods, and has potential applications in drug discovery, diagnostics, and biotechnology. Despite the significant advances in research on GlcNAc, several limitations and challenges still need to be addressed, and future directions in research on GlcNAc include the development of new analytical methods and tools, the identification of new roles and functions of GlcNAc in various biological processes, and the development of new GlcNAc-based products.

CAS Number577-76-4
Product Namebeta-D-glucosaminyl-(1->4)-aldehydo-D-glucosamine
IUPAC Name(2R,3R,4S,5R)-2-amino-4-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5,6-trihydroxyhexanal
Molecular FormulaC12H24N2O9
Molecular Weight340.33 g/mol
InChIInChI=1S/C12H24N2O9/c13-4(1-15)8(19)11(5(18)2-16)23-12-7(14)10(21)9(20)6(3-17)22-12/h1,4-12,16-21H,2-3,13-14H2/t4-,5+,6+,7+,8+,9+,10+,11+,12-/m0/s1
InChI KeyVUALREFPJJODHZ-JTCHKQLLSA-N
SMILESC(C1C(C(C(C(O1)OC(C(CO)O)C(C(C=O)N)O)N)O)O)O
Canonical SMILESC(C1C(C(C(C(O1)OC(C(CO)O)C(C(C=O)N)O)N)O)O)O
Isomeric SMILESC([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)N)O)N)O)O)O
CAS No: 577-76-4 Synonyms: Chitosan dimer dihydrochloride4-O-(b-D-Glucosamine)-D-glucosamine MDL No: MFCD06801377 Chemical Formula: C12H24N2O9·2HCl Molecular Weight: 413.25
References: 1. Agric. Biol. Chem., 1985, 98, p557


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