2'-O-Methylguanosine
[CAS# 2140-71-8]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 2'-O-Methylguanosine
• Synonyms: 2'-OMe-G
• Molecular Formula: C₁₁H₁₅N₅O₅
• Molecular Weight: 297.27
• Protein Sequence: N
• CAS Registry Number: 2140-71-8
• SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(NC3=O)N)CO)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2'-O-methylguanosine, often abbreviated as 2'-O-MeG, is a modified nucleoside that has attracted much attention due to its enhanced stability and unique biochemical properties. The compound represents a major advancement in nucleoside chemistry and has valuable applications in both research and therapeutic fields.

The discovery of 2'-O-methylguanosine is part of an effort to improve the stability and functionality of guanosine, an essential nucleoside involved in RNA synthesis and function. The modification involves the addition of a methyl group to the 2'-hydroxyl group of the ribose sugar in guanosine, which significantly enhances the resistance of the nucleoside to hydrolysis and enzymatic degradation.

The introduction of the 2'-O-methyl group was prompted by the need for more stable nucleoside analogs that can withstand harsh chemical environments and expand the practical applications of nucleoside-based compounds.

2'-O-methylguanosine is widely used to study the stability and structure of RNA. The 2'-O-methyl modification protects RNA from degradation by ribonucleases, making it easier to manipulate and analyze. Researchers use this modified guanosine to study RNA folding, interactions, and function, contributing to a deeper understanding of RNA biology.

In nucleic acid synthesis, 2'-O-MeG is used to produce stable RNA and DNA sequences. The enhanced stability of 2'-O-MeG allows for the synthesis of nucleic acids that are more resistant to degradation, which is critical for a variety of applications including the development of diagnostic assays and therapeutic nucleic acids.

The stability conferred by the 2'-O-methyl group makes 2'-O-MeG a promising candidate for the development of nucleoside therapeutics. By incorporating this modification, researchers can create more powerful nucleoside analogs for antiviral, anticancer, and gene therapy applications. These analogs benefit from improved pharmacokinetic profiles and reduced degradation in biological systems.

References

1980. Thermally induced biosynthesis of 2'-O-methylguanosine in tRNA from an extreme thermophile, Thermus thermophilus HB27. Proceedings of the National Academy of Sciences of the United States of America, 77(4).
DOI: 10.1073/pnas.77.4.1922

2021. The expanding world of tRNA modifications and their disease relevance. Nature reviews. Molecular cell biology, 22.
DOI: 10.1038/s41580-021-00342-0

2020. A metabolic labeling method detects m6A transcriptome-wide at single base resolution. Nature Chemical Biology, 16.
DOI: 10.1038/s41589-020-0526-9