N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methylcytidine
[CAS# 199593-08-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methylcytidine
• Synonyms: N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• Molecular Formula: C₃₃H₃₅N₃O₈
• Molecular Weight: 601.65
• CAS Registry Number: 199593-08-3
• SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O)OC

Properties

• Solubility: Insoluble (1.3E^-3 g/L) (25 °C), Calc.^*
• Density: 1.28±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

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

N-Acetyl-5'-O-[Bis(4-methoxyphenyl)benzyl]-2'-O-methylcytidine, abbreviated N-Ac-5'-O-[Bis(4-MP)PhMe]-2'-O-Me-Cyd, is a modified nucleoside with enhanced stability and utility in chemical and biological applications. The compound reflects advances in nucleoside chemistry aimed at improving the performance of nucleoside analogs in a variety of research and therapeutic settings.

The synthesis of N-Ac-5'-O-[Bis(4-MP)PhMe]-2'-O-Me-Cyd was developed to address the limitations of unmodified nucleosides, specifically their susceptibility to degradation and limited stability. By adding an acetyl group to the N-position of cytidine, a bis(4-methoxyphenyl)benzyl group to the 5' position, and a methyl group to the 2' position, the researchers designed a nucleoside with improved stability and functional properties.

The acetyl group at the N position enhances the nucleoside's resistance to hydrolysis, while the 5'-O-[Bis(4-MP)PhMe] group provides protection and improves handling during synthesis. The 2'-O-methyl modification increases the stability of the nucleoside against enzymatic degradation, making it more suitable for a variety of applications.

N-Ac-5'-O-[Bis(4-MP)PhMe]-2'-O-Me-Cyd is widely used in nucleic acid synthesis, including oligonucleotides. The bis(4-methoxyphenyl)benzyl protecting group at the 5' position promotes efficient and clean phosphoramidite chemistry, which is essential for automated synthesis of DNA and RNA. The 2'-O-methyl modification enhances the stability of the resulting nucleic acid, making it more robust and durable.

In RNA research, this nucleoside analog is used to study RNA stability and interactions. The improved stability provided by the 2'-O-methyl group makes it an excellent candidate for constructing stable RNA molecules. These stable RNA constructs are essential for understanding RNA structure, function, and interactions in various biological processes.

The stability and protective modifications of N-Ac-5'-O-[Bis(4-MP)PhMe]-2'-O-Me-Cyd make it potential in drug development. Modification of this compound can be used to design nucleoside analogs with improved pharmacokinetic properties and enhanced therapeutic effects. These nucleoside analogs have potential applications in antiviral, anticancer and genetic disease treatment.

References

none