53942-45-3 , Chitotriose undecaacetate;
Tri-N-acetyl-chitotriose octaacetate,
Cas:53942-45-3
C40H57N3O24 / 963.89
MFCD01862211
Tri-N-acetyl-chitotriose octaacetate
Chitotriose undecaacetate is a synthetic substrate that is used in transfecting experiments. It has high sensitivity and can be used to introduce nucleic acid into cells. Chitotriose undecaacetate is used as a synthetic fluorometric assay for the determination of chitinase activity in vitro or as a substrate for cell-free synthesis of nucleic acids. It has been shown to possess moieties that are sensitive to hydrogen chloride and chloride ions, making it an effective probe for the determination of these ions. Chitotriose undecaacetate also reacts with sephadex G-200, which makes it useful for separating DNA fragments by electrophoresis.
Chitotriose Undecaacetate (CUA) is a chitin derivative composed of three N-acetylglucosamine molecules, each with eleven acetate groups present on the C-3 and C-6 positions of the carbohydrate. Chitin is a natural polymer found in a variety of organisms, including insects, fungi, and crustaceans. CUA is synthesized from chitin, where the chitin is extracted from the organisms, and conversion is done in multiple stages. CUA is utilized in many scientific experiments as its unique structure gives it enormous potential for use in different applications, including pharmaceuticals, biotechnology, and material science.
Synthesis and Characterization
CUA is synthesized by the reaction of chitin with acetic anhydride in the presence of sodium acetate and acetic acid. The reaction results in the formation of CUA, which is then purified through multiple stages. The structure of CUA is confirmed through various analytical methods like Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and mass spectroscopy (MS).
Analytical Methods
FTIR, NMR, and MS are used to confirm the structure of CUA. Other analytical methods like high-performance liquid chromatography (HPLC), gas chromatography (GC), and thin-layer chromatography (TLC) are used for identification and separation of CUA from other compounds.
Biological Properties
Studies have shown that CUA exhibits antibacterial and antifungal properties, making it a potential candidate in the development of antimicrobial agents. CUA has also been found to have antitumor activity and has shown potential in cancer therapy.
Toxicity and Safety in Scientific Experiments
Studies have shown that CUA is non-toxic with no acute or chronic toxicity observed in animal models. However, studies on the long-term effects of CUA exposure are limited.
Applications in Scientific Experiments
CUA is utilized in various scientific experiments, including drug delivery systems, tissue engineering, and biomaterials. CUA has also been used in the development of biosensors, where it exhibits high specificity and sensitivity.
Current State of Research
Research on CUA is ongoing in various fields, including pharmaceuticals, biotechnology, and material science. Studies have shown that CUA has enormous potential in various applications, including drug delivery systems, tissue engineering, and biomaterials.
Potential Implications in Various Fields of Research and Industry
CUA has enormous potential in various fields, including biomaterials, where it can be used in the development of scaffolds for tissue engineering. CUA can also be used in the development of drug delivery systems, where it exhibits targeted and sustained release properties. Additionally, CUA can be utilized in the development of biosensors for detecting pathogens and environmental pollutants.
Limitations and Future Directions
CUA has limitations in its synthesis, and future research should focus on improving the synthesis process, increasing yields, and developing efficient methods for scale-up. Additionally, research should be conducted on the long-term effects of CUA exposure on human health. Future directions should also focus on exploring new potential applications of CUA in various fields.
Future Directions
Future research should explore the use of CUA in gene delivery systems, where it can be used as a carrier for gene therapy. Additionally, CUA can be utilized in the development of wound healing therapies, where it exhibits potential for promoting tissue regeneration. Research should also focus on developing green synthesis methods for CUA, where the process is eco-friendly and sustainable. Furthermore, studies should be conducted to understand the mechanism of action of CUA's antibacterial and antifungal properties, which can be utilized in the development of new antimicrobial agents.
CAS Number | 53942-45-3 |
Product Name | Chitotriose Undecaacetate |
IUPAC Name | [(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R)-5-acetamido-4,6-diacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-acetyloxyoxan-2-yl]methyl acetate |
Molecular Formula | C₄₀H₅₇N₃O₂₄ |
Molecular Weight | 963.89 |
InChI | InChI=1S/C40H57N3O24/c1-15(44)41-29-36(60-23(9)52)33(27(13-56-19(5)48)63-38(29)62-25(11)54)66-40-31(43-17(3)46)37(61-24(10)53)34(28(65-40)14-57-20(6)49)67-39-30(42-16(2)45)35(59-22(8)51)32(58-21(7)50)26(64-39)12-55-18(4)47/h26-40H,12-14H2,1-11H3,(H,41,44)(H,42,45)(H,43,46)/t26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38?,39+,40+/m1/s1 |
SMILES | CC(=O)NC1C(C(C(OC1OC2C(OC(C(C2OC(=O)C)NC(=O)C)OC(=O)C)COC(=O)C)COC(=O)C)OC3C(C(C(C(O3)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C)OC(=O)C |
Synonyms | O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-α-D-glucopyranose; Tri-N-acetyl Chitotriose Octaacetate; |
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