5-Methyl-2'-methoxyethoxycytosine
[CAS# 244105-55-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Cytosine
• Name: 5-Methyl-2'-methoxyethoxycytosine
• Synonyms: 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-methylpyrimidin-2-one
• Molecular Formula: C₁₃H₂₁N₃O₆
• Molecular Weight: 315.32
• Protein Sequence: N
• CAS Registry Number: 244105-55-3
• SMILES: CC1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)OCCOC

Properties

• Density: 1.52

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

5-Methyl-2'-methoxyethoxycytosine, abbreviated 5-Me-2'-O-ME-C, is a special nucleoside derivative known for its stability and versatility in biochemical and medical applications. The compound features a methyl group at the 5-position of the cytosine base and a 2'-methoxyethoxy group on the ribose sugar, which together enhance its properties.

5-Methyl-2'-methoxyethoxycytosine was developed to meet the need for more stable nucleoside analogs for research and therapeutic applications. The introduction of the 5-methyl group improves the nucleoside's resistance to deamination, while the 2'-methoxyethoxy modification improves stability and solubility. This combination is designed to create nucleosides with excellent performance in a variety of biochemical processes.

In RNA research, 5-methyl-2'-methoxyethoxycytosine is used to stabilize RNA molecules and protect them from enzymatic degradation. The 2'-methoxyethoxy modification enhances resistance to ribonucleases, making it easier to study RNA structure, function, and interactions. This stability is essential for producing reliable RNA probes and constructs for molecular biology studies.

Incorporating 5-methyl-2'-methoxyethoxycytosine into nucleic acid synthesis improves the stability and integrity of the resulting RNA and DNA sequences. This stability is particularly beneficial for creating oligonucleotides used in gene expression studies, diagnostic assays, and therapeutic nucleic acids. The enhanced properties of this modified nucleoside ensure that the synthesized molecules retain their functionality and longevity.

5-methyl-2'-methoxyethoxycytosine has potential for therapeutic development due to its stability and resistance to degradation. By incorporating this modification, researchers can design nucleoside analogs with enhanced pharmacokinetic characteristics for use in antiviral and anticancer treatments. These modified nucleosides can lead to more effective treatments with prolonged activity and reduced dosing frequency.

References

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