5,2'-O-Dimethyluridine
[CAS# 55486-09-4]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 5,2'-O-Dimethyluridine
• Synonyms: 2'-O-Methyl-5-methyluridine; 1-[(2R,3R,4R,5R)-4-Hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• Molecular Formula: C₁₁H₁₆N₂O₆
• Molecular Weight: 272.26
• Protein Sequence: N
• CAS Registry Number: 55486-09-4
• SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)OC

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.597, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

5,2'-O-Dimethyluridine is a chemical compound belonging to the family of modified nucleosides. It is a derivative of uridine, a naturally occurring nucleoside composed of the nitrogenous base uracil and the sugar ribose. The addition of two methyl groups, one at the 5-position of the uracil ring and another at the 2'-position of the ribose, differentiates this compound from its parent structure, uridine.

The discovery of 5,2'-O-dimethyluridine is linked to the broader research efforts focused on the modification of nucleosides to explore their effects on nucleic acids and their potential applications in various biological and chemical processes. Modifying the structure of nucleosides, such as uridine, allows for the study of their interactions with RNA and DNA, providing insights into their roles in cellular mechanisms and their potential therapeutic applications. These modifications can affect the stability, recognition, and reactivity of nucleosides in biochemical reactions, making them valuable tools for researchers.

5,2'-O-Dimethyluridine is used primarily in the fields of biochemistry and molecular biology. It has been utilized in studies involving RNA synthesis, where modified nucleosides like 5,2'-O-dimethyluridine are incorporated into RNA sequences to investigate their effects on RNA structure and function. The modification at the 2'-position of the sugar ring is particularly relevant, as this modification can influence the ribose’s conformation and interactions with other molecules. The presence of the dimethyl group at the 5-position of uracil is believed to influence the stability and base-pairing properties of the nucleoside.

In addition to its role in synthetic biology and RNA research, 5,2'-O-dimethyluridine has applications in the development of therapeutic agents. Modified nucleosides like 5,2'-O-dimethyluridine are often studied for their potential use in antiviral and anticancer treatments. These modified nucleosides can act as substrates for the synthesis of modified RNA or DNA molecules, which may exhibit enhanced resistance to degradation or increased efficacy in therapeutic applications. Their ability to influence the secondary structure of RNA and DNA also makes them useful in the design of oligonucleotides for gene silencing, gene editing, and other genetic interventions.

Furthermore, the incorporation of 5,2'-O-dimethyluridine into RNA molecules can improve the stability of the RNA, making it less susceptible to exonuclease degradation. This property is particularly advantageous when designing RNA-based therapeutics, such as small interfering RNA (siRNA) or messenger RNA (mRNA) vaccines, which require stability in biological systems for effective therapeutic action.

While 5,2'-O-dimethyluridine itself is not widely used as a drug, its application in research has contributed to the development of modified nucleoside-based therapies, especially in the context of RNA therapeutics. The study of nucleoside modifications continues to be a key area of research in both fundamental biology and applied medicine.

In summary, 5,2'-O-dimethyluridine is a modified nucleoside that has proven valuable in scientific research, particularly in the study of RNA structure and function. Its applications extend to the development of more stable RNA molecules for use in gene therapies and antiviral treatments. By incorporating modifications like those found in 5,2'-O-dimethyluridine, researchers are able to enhance the properties of nucleosides, advancing the field of nucleic acid-based therapeutics.

References

1974. 2′-O-Methyl ribothymidine: a component of rabbit liver lysine transfer RNA. Nucleic Acids Research, 1(1).
DOI: 10.1093/nar/1.1.35

2005. Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides. Bioorganic & Medicinal Chemistry, 13(24).
DOI: 10.1016/j.bmc.2005.07.046

2019. Structural and Energetic Effects of O2′-Ribose Methylation of Protonated Pyrimidine Nucleosides. Journal of The American Society for Mass Spectrometry, 30(11).
DOI: 10.1007/s13361-019-02300-9