1384570-83-5

Basic information

• Product Name: 5'-O-dimetoxytrityl-2-selenouridine
• Synonyms: 5'-O-dimetoxytrityl-2-selenouridine
• CAS NO: 1384570-83-5
• Molecular Weight: 609.537
• Mol File: 1384570-83-5.mol

Chemical Properties

• CAS DataBase Reference: 5'-O-dimetoxytrityl-2-selenouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-dimetoxytrityl-2-selenouridine(1384570-83-5)
• EPA Substance Registry System: 5'-O-dimetoxytrityl-2-selenouridine(1384570-83-5)

Safety Data

• Hazardous Substances Data: 1384570-83-5(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 7782-49-2 selenium 
• 1627601-87-9 5'-O-dimethoxytrityl-S-geranyl-2-thiouridine 
• 163496-06-8 5’-O-dimetoxytrityl-2-thiouridine 
• 20235-78-3 2-thiouridine 
• 1401688-09-2 S-geranyl-2-thiouridine 
• 1384570-81-3 C₃₁H₃₂N₂O₇S 

Downstream Products

• 1384570-93-7 C₃₉H₄₇N₃O₇SeSi 
• 1384570-90-4 C₃₉H₄₇N₃O₇SeSi 
• 1384570-85-7 5′-O-(4,4′-dimetoxytrityl)-2′-O-tert-butyldimethylsilyl-2-selenouridine 
• 1384570-88-0 C₃₆H₄₄N₂O₇SeSi 
• 1262964-71-5 C₄₈H₆₄N₅O₈PSeSi 

Relevant articles and documents

Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway

The newly discovered S-geranylated 2-thiouridines (geS2U) (Dumelin et al., 2012) and 2-selenouridines (Se2U) were recently shown to be synthesized by a single enzyme (selenouridine synthase, SelU) through two distinct pathways using the same 2-thiouridine substrate (S2U); however, no clear catalytic mechanism was proposed. We suggest that S-geranyl-2-thiouridine is an intermediate of the SelU-catalyzed conversion of S2U to Se2U. The successful chemical transformation of S2U → geS2U → Se2U is demonstrated here as an initial approximation of the intracellular pathway. The structure of Se2U was confirmed by spectroscopic methods, which included, for the first time, 77Se NMR data (δ 354 ppm).2014 Elsevier Inc. All rights reserved.

Novel RNA base air with higher specificity using single selenium atom

Specificity of nucleobase pairing provides essential foundation for genetic information storage, replication, transcription and translation in all living organisms. However, the wobble base pairs, where U in RNA (or T in DNA) pairs with G instead of A, might compromise the high specificity of the base pairing. The U/G wobble pairing is ubiquitous in RNA, especially in non-coding RNA. In order to increase U/A pairing specificity, we have hypothesized to discriminate against U/G wobble pair by tailoring the steric and electronic effects at the 2-exo position of uridine and replacing the 2-exo oxygen with a selenium atom. We report here the first synthesis of the 2-Se-U-RNAs as well as the 2-Se-uridine (SeU) phosphoramidite. Our biophysical and structural studies of the SeU-RNAs indicate that this single atom replacement can indeed create a novel U/A base pair with higher specificity than the natural one. We reveal that the SeU/A pair maintains a structure virtually identical to the native U/A base pair, while discriminating against U/G wobble pair. This oxygen replacement with selenium offers a unique chemical strategy to enhance the base pairing specificity at the atomic level.