5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(tert-butyl)dimethylsilyl]-N-(2-methyl-1-oxopropyl)guanosine
[CAS# 81279-39-2]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(tert-butyl)dimethylsilyl]-N-(2-methyl-1-oxopropyl)guanosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• Molecular Formula: C₄₁H₅₁N₅O₈Si
• Molecular Weight: 769.96
• CAS Registry Number: 81279-39-2
• SMILES: CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O)O[Si](C)(C)C(C)(C)C

Properties

• Density: 1.25

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(tert-butyl)dimethylsilyl]-N-(2-methyl-1-oxopropyl)guanosine is a complex guanosine derivative designed for advanced biochemical applications. Its unique modifications enhance stability and reactivity, making it a valuable tool in nucleic acid chemistry and molecular biology.

The compound was developed to address the stability and functionality limitations of traditional nucleosides used in biochemical applications. By combining protecting and modifying groups, the researchers aimed to create a guanosine analog with enhanced properties for synthetic and analytical purposes.

The chemical structure of 5'-O-[bis(4-methoxyphenyl)benzyl]-2'-O-[(tert-butyl)dimethylsilyl]-N-(2-methyl-1-oxopropyl)guanosine has several key modifications: 5'-O-[bis(4-methoxyphenyl)benzyl] protects the 5'-hydroxyl group, allowing for efficient and selective coupling during oligonucleotide synthesis; the 2'-O-[(tert-butyl)dimethylsilyl] protecting group stabilizes the 2'-hydroxyl group, preventing undesirable reactions and enhancing the overall stability of the compound; and the N-(2-methyl-1-oxopropyl) improves the analog's properties, such as its binding affinity and resistance to enzymatic degradation.

This compound is essential for the synthesis of high-quality RNA and DNA sequences. The protecting groups facilitate the sequential addition of nucleosides, allowing for precise formation of oligonucleotides.

By incorporating this guanosine analog, researchers can create modified nucleic acids with enhanced stability and functional properties. These modified nucleic acids are essential for the development of advanced therapeutics, including antisense oligonucleotides and RNA interference (RNAi) agents.

The enhanced stability and functional modifications of this compound make it ideal for studying nucleic acid interactions and enzyme mechanisms. It is used in a variety of biochemical assays, including binding studies and structural analysis, to gain insight into nucleic acid behavior and interactions.

References

none