54925-65-4

Usage

Uses

Used in Biomedical Research:
Uridine, 5'-O-[(1,1-dimethylethyl)dimethylsilyl]is used as a research tool for studying the structure and function of RNA molecules. The modification of uridine allows for better stability and pharmacokinetic properties, which can be advantageous in various experimental setups.
Used in Drug Delivery Systems:
Uridine, 5'-O-[(1,1-dimethylethyl)dimethylsilyl]is used as a component in drug delivery systems to improve the delivery and targeting of therapeutic agents. The enhanced ability to cross biological membranes can facilitate the transport of drugs to specific cells or tissues, potentially increasing the efficacy of treatments.
Used in Biotechnological Applications:
Uridine, 5'-O-[(1,1-dimethylethyl)dimethylsilyl]is used as a building block in the synthesis of modified nucleic acids for biotechnological purposes. The improved stability and pharmacokinetic properties of the modified uridine can be beneficial in the development of novel biomaterials and therapeutics.

Upstream product

• 1227248-63-6 C₂₀H₃₄N₂O₈Si 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 58-96-8 uridine 

Downstream Products

• 163254-10-2 1-<5'-O-(tert-Butyldimethylsilyl)-2'-O-cinnamoyl-3'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil 
• 163254-08-8 1-<5'-O-(tert-Butyldimethylsilyl)-3'-O-cinnamoyl-2'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil 
• 201664-47-3 O^5'-tert-butyldimethylsilyl-N³,O^2',O^3'-tribenzoyluridine 
• 820212-28-0 3-benzyl-1-[3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 820212-22-4 5'-O-tert-butyldimethylsilyl-2',3'-O-bis(benzyloxycarbonyl)uridine 
• 1205121-98-7 C₂₃H₃₄N₂O₇Si 
• 1315584-44-1 5'-O-[phenyl(ethoxy-L-alaninyl)phosphoryl]uridine 
• 1315584-43-0 5'-O-[phenyl(ethoxy-L-alaninyl)phosphoryl]-2',3'-O-bis(benzyloxycarbonyl)uridine 
• 1296160-60-5 C₄₂H₅₁N₄O₉P 
• 1296160-68-3 C₃₆H₃₅Br₂N₂O₁₁PS 
• 1296160-67-2 C₃₄H₃₁Br₂N₂O₁₁PS 
• 55798-09-9 2',3'-O,N³-tribenzoyluridine 
• 1259874-66-2 C₃₅H₃₃N₂O₁₄P 

Relevant academic research and scientific papers

A phosphate bound universal linker for DNA synthesis

A uridine-based linker immobilized onto polystyrene beads at the 5' terminus via a phosphodiester group and then used as a universal DNA synthesis support gives post synthesis DNA cleavage in 8 hrs or less without alkali metal salts. DNA produced with the new support was analyzed by HPLC, MALDI mass spectroscopy and PAGE. Each analysis showed DNA of equivalent quality to that produced with standard CPG supports, without contaminating materials resulting from linker or support backbone decomposition.

Lewis acid mediated reductive ring opening of 2-methoxyethylidene acetals: A new approach to 2-methoxyethyl (MOE) ethers of cis-diols

The reductive opening of 2-methoxyethylidene acetals of vicinal diols in uridine and 1,4-anhydro-D-ribitol in the presence of TiCl4 and Et3SiH was investigated. The 3′-O-(2-methoxyethyl) ether of uridine and the 2′-O-(2-methoxyethyl)

METHOD FOR SYNTHESIZING RIBONUCLEIC ACID H-PHOSPHONATE MONOMER, AND OLIGONUCLEOTIDE SYNTHESIS IN WHICH SAID MONOMER IS USED

The present invention pertains to a method for synthesizing a ribonucleic acid H-phosphonate monomer, and a method for performing oligonucleotide synthesis in which said monomer is used. The present invention pertains to a method for manufacturing an inex

Synthesis and in vitro growth inhibitory activity of novel silyl- and trityl-modified nucleosides

Seventeen silyl- and trityl-modified (5′-O- and 3′,5′-di-O-) nucleosides were synthesized with the aim of investigating the in vitro antiproliferative activities of these nucleoside derivatives. A subset of the compounds was evaluated at a fixed concentra

MONOMER FOR SYNTHESIS OF RNA, METHOD FOR PRODUCING SAME, AND METHOD FOR PRODUCING RNA

The objective of the present invention is to provide a monomer for RNA synthesis which can be efficiently produced and therefore by which the producing cost of RNA can be remarkably decreased, and a method for efficiently producing the monomer in a small number of steps. In addition, the objective of the present invention is also to provide a method by which RNA can be efficiently produced even when a approximately stoichiometry amount of the monomer for RNA synthesis is used. The monomer for RNA synthesis according to the present invention is represented by the following formula (I) or (I'): wherein R1 is a protective group of the hydroxy group and R2 is an alkyl group or the like.

MONOMER FOR SYNTHESIS OF RNA, METHOD FOR PRODUCING SAME, AND METHOD FOR PRODUCING RNA

The objective of the present invention is to provide a monomer for RNA synthesis which can be efficiently produced and therefore by which the producing cost of RNA can be remarkably decreased, and a method for efficiently producing the monomer in a small number of steps. In addition, the objective of the present invention is also to provide a method by which RNA can be efficiently produced even when a approximately stoichiometry amount of the monomer for RNA synthesis is used. The monomer for RNA synthesis according to the present invention is represented by the following formula (I) or (I′): wherein R1 is a protective group of the hydroxy group and R2 is an alkyl group or the like.

Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays Dedicated to Dr. Teruo Umemoto on the occasion of receiving the ACS Award for Creative Work in Fluorine Chemistry.

Analogs of ribonucleotides (RNA) stable to enzymatic hydrolysis were prepared and characterized. Computational investigations revealed that this class of compounds with a modified triphosphate exhibits the correct polarity and minimal steric effects compa

Bifunctional inhibition of HIV-1 reverse transcriptase: A first step in designing a bifunctional triphosphate

The onset of resistance to approved anti-AIDS drugs by HIV necessitates the search for novel inhibitors of HIV-1 reverse transcriptase (RT). Developing single molecular agents concurrently occupying the nucleoside and nonnucleoside binding sites in RT is an intriguing idea but the proof of concept has so far been elusive. As a first step, we describe molecular modeling to guide focused chemical syntheses of conjugates having nucleoside (d4T) and nonnucleoside (TIBO) moieties tethered by a flexible polyethylene glycol (PEG) linker. A triphosphate of d4T-6PEG-TIBO conjugate was successfully synthesized that is recognized as a substrate by HIV-1 RT and incorporated into a double-stranded DNA.

Efficient synthesis of exo-N-carbamoyl nucleosides: Application to the synthesis of phosphoramidate prodrugs

An efficient protection protocol for the 6-exo-amino group of purine nucleosides with various chloroformates was developed utilizing N-methylimidazole (NMI). The reaction of an exo-N6-group of adenosine analogue 1 with alkyl/and aryl chloroformates under optimized conditions provided the N6-carbamoyl adenosines (2a-j) in good to excellent yields. The reaction of N6-Cbz-protected nucleosides (5a-c) with phenyl phosphoryl chloride (7) using t-BuMgCl followed by catalytic hydrogenation afforded the corresponding phosphoramidate pronucleotides (8a-c) in excellent yield.

Design and synthesis of α-carboxy phosphononucleosides

Rhodium catalyzed O-H insertion reactions employing α- diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5′-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.