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
• Article Data: 3

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

5-Bromo-2''-O-methyluridine is an analog of Uridine (U829910) and is used as a reagent in the synthesis of RNA containing rigid and nonpertubing cytidine-derived spin labels.

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.

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