5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-N-(2-methyl-1-oxopropyl)guanosine
[CAS# 114745-26-5]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-N-(2-methyl-1-oxopropyl)guanosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-methoxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• Molecular Formula: C₃₆H₃₉N₅O₈
• Molecular Weight: 669.72
• CAS Registry Number: 114745-26-5
• 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)OC

Properties

• Solubility: Insoluble (3.1E^-4 g/L) (25 °C), Calc.^*
• Density: 1.35±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.641, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

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

Discovery and Applications

5'-O-[Bis(4-methoxyphenyl)benzyl]-2'-O-methyl-N-(2-methyl-1-oxopropyl)guanosine is a modified nucleoside with unique structural features that enhance its stability and functionality. The compound includes a protective bis(4-methoxyphenyl)benzyl (DMT) group at the 5' position, a methyl group at the 2' position of the ribose, and an N-acyl modification. These modifications make it a valuable tool in nucleic acid synthesis and therapeutic development.

The development of 5'-O-[Bis(4-methoxyphenyl)benzyl]-2'-O-methyl-N-(2-methyl-1-oxopropyl)guanosine is part of an ongoing effort to improve nucleoside chemistry. The DMT group at the 5' position protects the nucleoside during oligonucleotide synthesis, ensuring precise and efficient assembly. The 2'-O-methyl modification increases resistance to enzymatic degradation and enhances stability. The N-acyl group further stabilizes the nucleoside and may improve its biological activity.

Modifications in 5'-O-[bis(4-methoxyphenyl)benzyl]-2'-O-methyl-N-(2-methyl-1-oxopropyl)guanosine enhance its performance in nucleic acid synthesis and therapy. The DMT group prevents unwanted reactions at the 5' position during synthesis. The 2'-O-methyl group protects the nucleoside from degradation by ribonucleases, enzymes that normally degrade RNA. The N-acyl group adds further stability and may affect the interaction of the nucleoside with other molecules.

The main application of this modified nucleoside is the automated synthesis of oligonucleotides. The DMT group facilitates the stepwise construction of oligonucleotides by protecting the 5' hydroxyl group, ensuring accurate and efficient assembly. This is critical for generating DNA and RNA sequences for research and therapy.

The 2'-O-methyl and N-acyl modifications enhance the stability and efficacy of RNA therapeutics such as small interfering RNA (siRNA) and antisense oligonucleotides. These modifications increase resistance to enzymatic degradation and improve the activity and longevity of the therapeutic molecule in vivo. This makes them more effective in gene regulation and disease treatment.

In molecular biology, this compound is used to study RNA structure and function. Its enhanced stability allows for detailed studies of RNA interactions and mechanisms, advancing the understanding of genetic regulation and RNA-based technologies.

The main advantages of 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-N-(2-methyl-1-oxopropyl)guanosine are its stability and functionality. The DMT group ensures precise oligonucleotide synthesis, while the 2'-O-methyl and N-acyl modifications enhance stability and bioactivity. These properties make it an indispensable tool for research and therapeutic applications.

Despite the benefits of this compound, there are challenges to its use. The synthesis of this modified nucleoside can be complex and costly. Furthermore, while these modifications improve stability, they can also affect the bioactivity and delivery of RNA therapeutics, requiring careful design and optimization in therapeutic applications.

References

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