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7699-38-9 ,4-Nitrophenyl N,N'',N''' -triacetyl-b-D-chitotriose, CAS:7699-38-9

7699-38-9 ,4-Nitrophenyl N,N'',N''' -triacetyl-b-D-chitotriose,
CAS:7699-38-9
C30H44N4O18 / 748.69
MFCD00057914

4-Nitrophenyl N,N',N''-triacetyl-b-D-chitotriose

4-Nitrophenyl beta-D-N,N',N''-triacetylchitotriose (NP-chitotriose) is a chitin oligosaccharide that has gained significant attention for its applications in various fields of research and industry. In this paper, we aim to provide a comprehensive overview of NP-chitotriose, including 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.

Definition and Background:

Chitin is a linear polysaccharide that is found in the cell wall of fungi, the exoskeleton of insects and crustaceans, and the cuticle of other arthropods. Chitotriose is a trimer of N-acetylglucosamine (GlcNAc) and is the smallest unit of chitin. NP-chitotriose is a derivative of chitotriose in which the hydroxyl group at position 6 of GlcNAc is replaced by a nitrophenyl group. NP-chitotriose has been extensively studied for its applications in various areas of research and industry, including carbohydrate chemistry, enzymology, and drug delivery.

Synthesis and Characterization:

NP-chitotriose can be synthesized by the acetylation of chitotriose with acetic anhydride and 4-nitrophenol in the presence of a catalyst. The reaction can be monitored by thin-layer chromatography (TLC) and characterized by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.

Analytical Methods:

NP-chitotriose can be analyzed by TLC, high-performance liquid chromatography (HPLC), NMR spectroscopy, mass spectrometry, and capillary electrophoresis. These methods can be used to confirm the purity and identity of the compound.

Biological Properties:

NP-chitotriose has been shown to be an inhibitor of chitinases, enzymes that break down chitin. It has also been shown to bind to chitin-binding proteins and lectins, which are involved in various biological processes. NP-chitotriose has potential applications as an antimicrobial agent, an immunomodulator, and a drug delivery vehicle.

Toxicity and Safety in Scientific Experiments:

Studies have shown that NP-chitotriose is non-toxic to mammalian cells in vitro and has a low toxicity in vivo. However, as with any chemical, it should be handled with care and proper safety precautions should be taken when working with it.

Applications in Scientific Experiments:

NP-chitotriose has a wide range of applications in various fields of research and industry. It has been used as a substrate for chitinases and other chitin-degrading enzymes, as a ligand for chitin-binding proteins and lectins, and as a scaffold for drug delivery systems. It has also been used in studies of chitin biosynthesis and degradation, as well as in the development of diagnostic assays for chitinases and chitin-binding proteins.

Current State of Research:

Research on NP-chitotriose is ongoing, with a focus on its biological and pharmaceutical applications. Recent studies have explored the use of NP-chitotriose as an immunomodulator, an inhibitor of chitinases in asthma, and a scaffold for the delivery of anticancer drugs.

Potential Implications in Various Fields of Research and Industry:

NP-chitotriose has potential implications in various fields of research and industry, including carbohydrate chemistry, enzymology, immunology, and drug delivery. Its ability to inhibit chitinases makes it a potential therapeutic agent for diseases involving chitin deposition, such as asthma and fungal infections. Its use as a scaffold for drug delivery systems could lead to the development of more effective and targeted therapies for cancer and other diseases.

Limitations and Future Directions:

Despite its potential applications, NP-chitotriose has some limitations. Its synthesis requires specialized equipment and expertise, and its stability and solubility can be problematic under certain conditions. Future research is needed to address these limitations and explore the full potential of NP-chitotriose. Some potential future directions include the development of more efficient synthesis methods, the exploration of its immunomodulatory effects, and the investigation of its potential use in tissue engineering and regenerative medicine.

In conclusion, NP-chitotriose is a chitin oligosaccharide with a wide range of potential applications in various fields of research and industry. Its physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications, current state of research, potential implications, limitations, and future directions have been discussed in this paper. Further research is needed to fully explore the potential of NP-chitotriose and its implications in multiple fields.

CAS Number7699-38-9
Product Name4-Nitrophenyl beta-D-N,N',N''-triacetylchitotriose
IUPAC NameN-[2-[5-acetamido-6-[5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Molecular FormulaC30H44N4O18
Molecular Weight748.69 g/mol
InChIInChI=1S/C30H44N4O18/c1-11(38)31-19-23(42)22(41)16(8-35)48-29(19)51-27-18(10-37)50-30(21(25(27)44)33-13(3)40)52-26-17(9-36)49-28(20(24(26)43)32-12(2)39)47-15-6-4-14(5-7-15)34(45)46/h4-7,16-30,35-37,41-44H,8-10H2,1-3H3,(H,31,38)(H,32,39)(H,33,40)
InChI KeyUWYYAJFSFHIFNY-UHFFFAOYSA-N
SMILESCC(=O)NC1C(C(C(OC1OC2C(OC(C(C2O)NC(=O)C)OC3C(OC(C(C3O)NC(=O)C)OC4=CC=C(C=C4)[N+](=O)[O-])CO)CO)CO)O)O
Canonical SMILESCC(=O)NC1C(C(C(OC1OC2C(OC(C(C2O)NC(=O)C)OC3C(OC(C(C3O)NC(=O)C)OC4=CC=C(C=C4)[N+](=O)[O-])CO)CO)CO)O)O
CAS No: 7699-38-9 MDL No: MFCD00057914 Chemical Formula: C30H44N4O18 Molecular Weight: 748.69
References: 1. Osawa T, Nakazawa Y, Biochim. Biophys. Acta 1966, 130, 56


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