34218-83-2

Basic information

• Product Name: 5-BroMo-2'-O-Methyluridine
• Synonyms: 5-BroMo-2'-O-Methyluridine;5-Br-2'-OMe-U
• CAS NO: 34218-83-2
• Molecular Formula: C₁₀H₁₃BrN₂O₆
• Molecular Weight: 337.12402
• Mol File: 34218-83-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-BroMo-2'-O-Methyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BroMo-2'-O-Methyluridine(34218-83-2)
• EPA Substance Registry System: 5-BroMo-2'-O-Methyluridine(34218-83-2)

Safety Data

• Hazardous Substances Data: 34218-83-2(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology and Biochemistry:
5-Bromo-2'-O-methyluridine is used as a reagent for the synthesis of RNA containing rigid and nonperturbing cytidine-derived spin labels. The incorporation of 5-Bromo-2'-O-methyluridine into RNA molecules enables the study of their structure, dynamics, and interactions with other biomolecules, which is crucial for understanding the fundamental processes of life.
In the Synthesis of Modified Nucleic Acids:
5-Bromo-2'-O-methyluridine is also utilized in the synthesis of modified nucleic acids, which are essential for various biotechnological and therapeutic applications. These modified nucleic acids can be used for the development of novel drugs, gene therapies, and diagnostic tools.
In Research and Development:
5-Bromo-2'-O-methyluridine is a valuable tool in research and development, particularly in the fields of molecular biology, biochemistry, and pharmaceuticals. It can be used to study the effects of structural modifications on the properties and functions of nucleic acids, leading to the discovery of new biological insights and potential applications.
In the Pharmaceutical Industry:
5-Bromo-2'-O-methyluridine may be used in the pharmaceutical industry for the development of new drugs targeting RNA molecules. Its unique properties make it a promising candidate for the design of novel therapeutic agents that can modulate RNA function and potentially treat various diseases.
In the Diagnostics Industry:
5-Bromo-2'-O-methyluridine can also be employed in the development of diagnostic tools that rely on the detection and analysis of RNA molecules. Its incorporation into RNA can enhance the sensitivity and specificity of diagnostic assays, leading to more accurate and reliable results.

Upstream product

• 2140-76-3 2'-O-methyluridine 
• 1391914-06-9 5-bromo-3',5'-O-benzoyl-2'-O-methyluridine 
• 632367-79-4 1,3,5-di-O-benzoyl-2-O-methyl-α/β-D-ribofuranose 

Downstream Products

• 1391914-07-0 C₃₁H₃₁BrN₂O₈ 
• 1188522-81-7 3',5'-diacetyl-5-bromo-2'-O-methyluridine 
• 1393486-73-1 C₅₂H₆₄N₆O₁₀P 
• 1393486-78-6 C₄₃H₄₅N₄O₉ 

Relevant articles and documents

An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI)

An efficient and facile strategy has been developed for bromination of nucleosides using sodium monobromoisocyanurate (SMBI). Our methodology demonstrates bromination at the C-5 position of pyrimidine nucleosides and the C-8 position of purine nucleosides. Unprotected and also several protected nucleosides were brominated in moderate to high yields following this procedure.

Synthesis and characterization of RNA containing a rigid and nonperturbing cytidine-derived spin label

The nitroxide-containing nucleoside Cm is reported as the first rigid spin label for paramagnetic modification of RNA by solid-phase synthesis. The spin label is well accommodated in several RNA secondary structures as judged by its minor effect on the thermodynamic stability of hairpin and duplex RNA. Electron paramagnetic resonance (EPR) spectroscopic characterization of mono-, bi-, and trimolecular RNA structures shows that Cm will be applicable for advanced EPR studies to elucidate structural and dynamic aspects of folded RNA.

Tritium labeling of full-length small interfering RNAs

A simple procedure is described for full-length single internal [ 3H]-radiolabeling of oligonucleotides. Previous labeling strategies have been applied to large molecular weight compounds such as proteins and oligonucleotides, for example, iodination and 111In labeling via covalently bounded chelators. However, a procedure has not yet been reported for single internal radiolabeling of oligonucleotides that preserves the molecular structure (3H replacing a 1H). In following our strategy, the radiolabel can be strategically placed within a stable and predetermined internal position of the siRNA. This placement was accomplished by placing a 5-bromouridine or 5-bromo-2'-O-methyluridine phosphoramidite building block into the middle of the antisense strand using standard phosphoramidite chemistry. The deprotected full-length antisense strand was tritium labeled by bromine/tritium exchange, catalyzed by palladium on charcoal in the predetermined 5-position of either uridine or 2'-O-methyluridine. Internal placement of the building block within the oligonucleotide sequence and label placement at 5-position decreases the likelihood of the label to be readily cleaved from the oligonucleotide in vivo, and loss of the label by spontaneous tritium/hydrogen exchange. The tritiated single-stranded and double-stranded RNAs were also shown to be radio and chemically stable for at least 6 months at -80 °C. This allows more than sufficient time to conduct pharmaceutical formulation and pharmacokinetic studies. Copyright