41708-93-4, Chitotriose 3HCl,
CAS:41708-93-4
C12H24N2O9•3HCl /
Chitintriose, also known as N,N'-Diacetylchitobiose, is a small molecule composed of two N-acetyl-D-glucosamine units linked by a β-1,4-glycosidic bond. This molecule is an important building block in the chitin synthesis pathway in various organisms. Chitinases, which are enzymes that break down chitin, release chitintriose during the chitin degradation process. Chitintriose has attracted attention due to its biological properties and potential applications in various fields of research and industry.
Physical and Chemical Properties:
Chitintriose has a molecular weight of 425 g/mol and a melting point of 184-186°C. It is a white to off-white powder that is soluble in water and acetic acid. Chitintriose is stable at pH ranges from 3 to 8, and it can be hydrolyzed in acidic conditions.
Synthesis and Characterization:
Chitintriose can be synthesized by enzymatic hydrolysis of chitin or by chemical synthesis. Enzymatic hydrolysis is preferred due to the high purity of the product. The characterization of chitintriose is mainly done by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS).
Analytical Methods:
Chitintriose can be analyzed using various methods, including high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE).
Biological Properties:
Chitintriose has been shown to induce apoptosis in cancer cells through the activation of caspase-3 and caspase-8 pathways. It also has immunostimulatory effects and promotes the activation of macrophages and dendritic cells. Chitintriose has antimicrobial properties and can inhibit the growth of various microorganisms, including bacteria, fungi, and viruses.
Toxicity and Safety in Scientific Experiments:
Chitintriose has low toxicity and is considered safe for use in scientific experiments. However, it is important to use proper safety measures and follow good laboratory practices when handling chitintriose.
Applications in Scientific Experiments:
Chitintriose has various applications in scientific experiments, including as a substrate for chitinase assays, as a ligand for lectin assays, and as an inducer for apoptosis in cancer cell lines. It is also used as an immunostimulant and antimicrobial agent in biological research.
Current State of Research:
Research on chitintriose is mainly focused on its biological properties and potential applications in various fields of research and industry. Recent studies have explored the use of chitintriose as an adjuvant for vaccine development, as a biocontrol agent for crop protection, and as a potential agent for cancer therapy.
Potential Implications in Various Fields of Research and Industry:
Chitintriose has potential implications in various fields of research and industry, including biotechnology, agriculture, and medicine. It can be used as a component in the development of new drugs, vaccines, and anti-microbial agents. It can also be used in the production of chitin-based materials, such as biodegradable plastics and scaffolds for tissue engineering.
Limitations and Future Directions:
Although chitintriose has shown promising results in various studies, its potential applications and limitations are still under investigation. Future studies should focus on the stability, toxicity, and biocompatibility of chitintriose, as well as its potential applications in different fields of research and industry. Some potential future directions are:
- Investigating the use of chitintriose as a potential drug delivery system.
- Exploring the effect of chitintriose on the gut microbiome and its potential applications in gut health.
- Studying the impact of chitintriose on the environment and its potential use in waste management.
- Investigating the use of chitintriose in the production of new materials with improved properties.
- Developing new analytical methods for the detection and quantification of chitintriose in different biological and environmental samples.
CAS Number | 41708-93-4 |
Product Name | Chitintriose |
IUPAC Name | (2R,3R,4S,5R)-2-amino-4-[(2S,3R,4R,5S,6R)-3-amino-5-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5,6-trihydroxyhexanal |
Molecular Formula | C18H35N3O13 |
Molecular Weight | 501.5 g/mol |
InChI | InChI=1S/C18H35N3O13/c19-5(1-22)11(27)15(6(26)2-23)33-18-10(21)14(30)16(8(4-25)32-18)34-17-9(20)13(29)12(28)7(3-24)31-17/h1,5-18,23-30H,2-4,19-21H2/t5-,6+,7+,8+,9+,10+,11+,12+,13+,14+,15+,16+,17-,18-/m0/s1 |
InChI Key | HBAVVSYNWHLVDB-UDAFUQIYSA-N |
SMILES | C(C1C(C(C(C(O1)OC2C(OC(C(C2O)N)OC(C(CO)O)C(C(C=O)N)O)CO)N)O)O)O |
Synonyms | chitintriose, chitotriose, chitotrisaccharide |
Canonical SMILES | C(C1C(C(C(C(O1)OC2C(OC(C(C2O)N)OC(C(CO)O)C(C(C=O)N)O)CO)N)O)O)O |
Isomeric SMILES | C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)N)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)N)O)CO)N)O)O)O |
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