2'-O-Methyluridine
[CAS# 2140-76-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 2'-O-Methyluridine
• Synonyms: 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidine-2,4-dione
• Molecular Formula: C₁₀H₁₄N₂O₆
• Molecular Weight: 258.23
• Protein Sequence: N
• CAS Registry Number: 2140-76-3
• EC Number: 966-056-1
• SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2'-O-methyluridine, abbreviated as 2'-O-MeU, is an important nucleoside analog with enhanced stability and versatility. This modified uridine derivative has attracted much attention for its beneficial properties in various biochemical and medical applications.

2'-O-methyluridine was developed to address the limitations of standard uridine in nucleic acid research and therapeutic applications. The addition of a methyl group to the 2'-hydroxyl group of the ribose sugar in uridine improves its chemical stability and resistance to degradation. This modification was introduced to enhance the durability of nucleic acids and optimize their performance in research and therapeutic settings.

In RNA research, 2'-O-methyluridine is used to stabilize RNA molecules against enzymatic degradation. The 2'-O-methyl modification prevents destruction by ribonucleases, allowing researchers to more reliably study RNA structure and function. This stability is essential for the synthesis of stable RNA probes and constructs for functional studies and diagnostic assays.

The addition of 2'-O-MeU to nucleic acid synthesis enhances the stability and longevity of the resulting RNA and DNA sequences. This stability is particularly valuable in the production of oligonucleotides for a variety of applications, including gene expression studies, therapeutic nucleic acids, and RNA-based vaccines. The use of 2'-O-MeU ensures that these molecules remain intact and functional for extended periods of time.

2'-O-methyluridine has potential in the development of nucleoside-based therapeutics. Its improved stability could be used to create more effective antiviral and anticancer agents. By incorporating 2'-O-MeU into therapeutic nucleosides, researchers can design drugs with enhanced pharmacokinetic properties and prolonged activity, potentially leading to better therapeutic efficacy and less frequent dosing.

References

1981. Purification and properties of several transfer RNA methyltransferases from S. typhimurium. Molecular and Cellular Biochemistry, 36(2).
DOI: 10.1007/bf02354908

2023. Methods to Analyze Post-transcriptional Modifications Applied to Stable RNAs in Staphylococcus aureus. RNA Structure and Function.
DOI: 10.1007/978-3-031-36390-0_11

2019. Antisense Oligonucleotides for the Treatment of Inner Ear Dysfunction. Neurotherapeutics, 16(2).
DOI: 10.1007/s13311-019-00729-0