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7531-49-9 , N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside

7531-49-9 , N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside ,
2-(Acetylamino)-2-deoxy-4-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl]-a-D-glucopyranosyl chloride 3,6-diacetate; 2-Acetamido-4-O-(2-acetamido-2-deoxy-b-D-glucopyranosyl)-2-deoxy-glucopyranosyl chloride 3,3',4',6,6'-pentaacetate
Cas:7531-49-9
C26H37ClN2O15 / 653.03
MFCD09840401

N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside , 

2-(Acetylamino)-2-deoxy-4-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl]-a-D-glucopyranosyl chloride 3,6-diacetate; 2-Acetamido-4-O-(2-acetamido-2-deoxy-b-D-glucopyranosyl)-2-deoxy-glucopyranosyl chloride 3,3',4',6,6'-pentaacetate

N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside is a galactosyltransferase inhibitor. It prevents the enzymatic transfer of a sugar group from UDP-galactose to an acceptor molecule by binding to the enzyme. N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside inhibits the enzymatic galactosylation of glycoproteins in cells and has been shown to be effective against bacterial strains resistant to other antibiotics. This drug is also chemoenzymatically synthesized using enzymes and chemical reagents.

N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside, also known as DAPC, is a highly complex carbohydrate molecule that has recently garnered attention in the research community. This paper aims to provide a comprehensive overview of DAPC, covering its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions for research.

Physical and Chemical Properties

N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside has a molecular weight of approximately 1390 g/mol and a complex three-dimensional structure. The molecule is a white crystalline powder, which is sparingly soluble in water, but readily soluble in organic solvents such as chloroform and methanol. The physical and chemical properties of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside are largely determined by its acetylation and chlorination status, as well as its complex three-dimensional structure.

Synthesis and Characterization

N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside is a highly complex molecule that is not synthesized by living organisms. Instead, it is typically synthesized in the laboratory using chemical or enzymatic methods. One of the most common methods for synthesizing N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside involves the reaction of chitin with acetic anhydride and acetyl chloride in the presence of a Lewis acid catalyst. This reaction results in the acetylation of the chitin molecule at the 3,6,3',4', and 6' positions of the glucosamine residues. Chlorination of the molecule is typically achieved using thionyl chloride.

The characterization of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside is typically performed using a variety of analytical techniques, including IR spectroscopy, NMR spectroscopy, and mass spectrometry. These techniques provide information about the structure of the molecule, including the location of the acetyl groups and the chlorination site.

Analytical Methods

Analytical methods for the detection of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside include mass spectrometry, NMR spectroscopy, and IR spectroscopy. Mass spectrometry provides accurate information about the molecular weight of the molecule, while NMR spectroscopy provides information about the structure of the molecule, including the position of the acetyl groups and the chlorination site. IR spectroscopy is used to detect the presence of specific functional groups, including the acetyl and chloro groups.

Biological Properties

The biological properties of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside are largely unknown, although preliminary studies suggest that it may have potential as an immunomodulatory agent. This is thought to be due to the unique structure of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside, which allows it to interact with immune cells and modulate their activity.

Toxicity and Safety in Scientific Experiments

There is limited information on the toxicity and safety of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside in scientific experiments. However, based on its chemical and physical properties, it is likely that N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside is relatively safe when handled appropriately. Nonetheless, proper safety measures should be employed when handling N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside in a laboratory setting.

Applications in Scientific Experiments

N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside has a limited range of applications in scientific experiments. However, it is thought to have potential as an immunomodulatory agent, which may be useful in the treatment of a range of diseases. Additionally, N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside may have potential as a tool for studying the structure and function of complex carbohydrates.

Current State of Research

The current state of research on N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside is relatively limited, with most studies focusing on its synthesis and characterization. However, there is growing interest in the potential applications of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside in the fields of immunology and carbohydrate chemistry.

Potential Implications in Various Fields of Research and Industry

The potential implications of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside in various fields of research and industry are largely unknown. However, it is thought that N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside may have applications as an immunomodulatory agent, which may have potential in the treatment of a range of diseases. Additionally, N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside may have potential applications in the field of carbohydrate chemistry.

Limitations and Future Directions

There are several limitations to the current research on N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside, including a lack of understanding of its biological properties and limited applications in scientific experiments. Future studies should focus on elucidating the biological properties of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside and exploring its potential as a therapeutic agent. Additionally, further research is needed to better understand the complexities of carbohydrate chemistry and the potential applications of N,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside in this field.

CAS Number7531-49-9
Product NameN,N'-Diacetyl-3,6,3',4',6'-penta-O-acetyl-1-chlorochitobioside
IUPAC Name[(3S,6S)-5-acetamido-6-[(3S,6R)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-chlorooxan-3-yl]oxy-3,4-diacetyloxyoxan-2-yl]methyl acetate
Molecular FormulaC₂₆H₃₇ClN₂O₁₅
Molecular Weight653.03
InChIInChI=1S/C26H37ClN2O15/c1-10(30)28-19-23(40-15(6)35)22(17(42-25(19)27)8-37-12(3)32)44-26-20(29-11(2)31)24(41-16(7)36)21(39-14(5)34)18(43-26)9-38-13(4)33/h17-26H,8-9H2,1-7H3,(H,28,30)(H,29,31)/t17?,18?,19?,20?,21-,22-,23?,24?,25+,26+/m1/s1
SMILESCC(=O)NC1C(C(C(OC1OC2C(OC(C(C2OC(=O)C)NC(=O)C)Cl)COC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
Synonyms2-(Acetylamino)-2-deoxy-4-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-α-D-glucopyranosyl Chloride 3,6-Diacetate; 2-Acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-glucopyranosyl Chloride 3,3’,4’,6,6’-Pentaacetate;


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