Category
2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine

Product Details
Product Name: | 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine |
2'3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine is a synthetic nucleoside analogue that belongs to the category of 5-fluorocytidine derivatives. This compound is structurally modified from the natural nucleoside cytidine, featuring several key alterations that enhance its chemical and biological properties. Notably, it incorporates a fluorine atom at the 5-position of the cytosine base, making it a fluorinated cytidine. Additionally, it is acetylated at both the 2' and 3' positions of the ribose sugar, classifying it as an acetylated nucleoside. The removal of the hydroxyl group at the 5' position further distinguishes it as a 5'-deoxy derivative.
Chemical Structure and Properties
The chemical formula for 2'3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine is C13H16FN3O6. Its molecular structure includes a cytosine base with a fluorine atom attached at the 5-position, a ribose sugar that is acetylated at the 2' and 3' positions, and lacks a hydroxyl group at the 5' position. These modifications collectively contribute to its unique chemical characteristics.
Biological Significance
As a modified cytidine analogue, 2'3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine exhibits potential as an antiviral and anticancer agent. The introduction of fluorine at the 5-position of cytosine can enhance the compound's metabolic stability and binding affinity to cellular targets. Acetylation at the 2' and 3' positions may further protect the nucleoside from enzymatic degradation, thereby prolonging its half-life in biological systems. The absence of the 5' hydroxyl group can alter its interaction with enzymes involved in nucleoside metabolism, potentially leading to distinct biological activities compared to its parent compound, cytidine.
Applications in Research and Therapeutics
Given its unique structural features and density, 2'3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine is of considerable interest in various fields of research. In medicinal chemistry, it serves as a valuable tool for studying the effects of nucleoside modifications on biological activity. Its potential as an antiviral agent is being explored, particularly against viruses that rely on cytidine metabolism for replication. Moreover, its anticancer properties are under investigation, as modified nucleosides can interfere with DNA synthesis and repair mechanisms in cancer cells.
In conclusion, 2'3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine represents a promising modified cytidine analogue with distinctive chemical properties, including a density above 5%. Its structural modifications—fluorination at the 5-position, acetylation at the 2' and 3' positions, and deoxygenation at the 5' position—confer unique biological activities that make it a valuable compound for both research and therapeutic applications. Further studies are essential to fully elucidate its mechanisms of action and potential clinical uses.


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