2'-O-(2-Methoxyethyl)-5-methyluridine
[CAS# 163759-49-7]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 2'-O-(2-Methoxyethyl)-5-methyluridine
• Synonyms: 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• Protein Sequence: N
• Molecular Formula: C₁₃H₂₀N₂O₇
• Molecular Weight: 316.31
• CAS Registry Number: 163759-49-7
• SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)OCCOC

Properties

• Density: 1.41

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H320-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

2'-O-(2-methoxyethyl)-5-methyluridine is an advanced nucleoside analog that is notable for its unique chemical modifications that enhance its stability and functional properties. This compound, often abbreviated as 2'-O-(2-ME)-5-MeU, represents a major advance in nucleoside chemistry and has promising applications in molecular biology and therapeutic development.

The development of 2'-O-(2-ME)-5-MeU stems from the need to improve the stability and efficacy of nucleoside therapeutics. Modification of the 2' position of the ribose ring with a 2-methoxyethyl group is intended to protect the nucleoside from enzymatic degradation and enhance its cellular uptake. Addition of a methyl group at the 5-position of the uridine base further improves its stability and bioactivity.

The synthesis of this compound involves attachment of the 2-methoxyethyl group via a selective glycosylation reaction followed by methylation of the uridine base. These modifications are intended to improve the compound's performance in biological systems and its potential as a therapeutic agent.

2'-O-(2-ME)-5-MeU has shown promise in antiviral and anticancer research due to its enhanced stability and ability to inhibit nucleic acid synthesis. Its chemical structure enables it to evade degradation by nucleoside metabolizing enzymes, making it a more effective inhibitor of viral and cancer cell proliferation. Researchers are exploring its potential for treating viral infections and various cancers by targeting specific nucleic acid pathways.

In RNA research, 2'-O-(2-ME)-5-MeU is used as a modified nucleoside for studying RNA stability and function. The methoxyethyl modification helps to increase the resistance of RNA molecules to nucleases, making it a valuable tool for building stable RNA-based therapeutics and diagnostics. This stability is essential for the development of RNA therapeutics that need to have long-term activity and reliability in clinical applications.

The unique structural features of this compound make it a candidate for drug design, especially in the development of nucleoside analogs with improved pharmacokinetic and pharmacodynamic properties. The enhanced stability and bioavailability of 2'-O-(2-ME)-5-MeU could lead to more effective drugs with fewer side effects, offering new possibilities for treating a range of diseases.

References

2009. Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF. Green Chemistry, 11(6), 855�862.
DOI: 10.1039/b818992g

2015. An efficient method for the synthesis of selenium modified nucleosides: its application in the synthesis of Se-adenosyl-L-selenomethionine (SeAM). Organic & Biomolecular Chemistry, 13(36), 9417�9427.
DOI: 10.1039/c5ob01326c

2024. Nucleic acid degradation as barrier to gene delivery: a guide to understand and overcome nuclease activity. Chemical Society Reviews, 53(1), 360�392.
DOI: 10.1039/d3cs00506b