BETA-PSEUDOURIDINE

Base Information

• Chemical Name: BETA-PSEUDOURIDINE
• CAS No.: 1445-07-4
• Molecular Formula: C9H12N2O6
• Molecular Weight: 244.204
• NSC Number: 162405
• Mol file: 1445-07-4.mol

Synonyms:Uracil,5-b-D-ribofuranosyl- (6CI,7CI,8CI);5-(b-D-Ribofuranosyl)uracil;5-Ribosyluracil;NSC 162405;Pseudouridine;Pseudouridine C;b-D-Pseudouridine;b-Pseudouridine;y-Uridine;

Chemical Property of BETA-PSEUDOURIDINE

Chemical Property:

• Vapor Pressure: 3.63E-15mmHg at 25°C
• Melting Point: 222 °C
• Refractive Index: 1.623
• Boiling Point: 598.4 °C at 760 mmHg
• PKA: 8.52±0.10(Predicted)
• Flash Point: 315.7 °C
• PSA: 135.64000
• Density: 1.641 g/cm³
• LogP: -2.78280
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Methanol (Very Slightly, Heated), Water (Slightly, Sonicated, Heated)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 244.06953611
• Heavy Atom Count: 17
• Complexity: 382

Purity/Quality:

98% ^*data from raw suppliers

Pseudouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)C2C(C(C(O2)CO)O)O
• Description: β-Pseudouridine is the C-5 glycoside isomer of the nucleoside uridine . It is formed when uridine in RNA undergoes site-specific isomerization by a pseudouridine synthase enzyme. β-pseudouridine is found in tRNAs from bacteria, archaea, and eukaryotes. In vitro, it reduces the number of X-ray-induced chromosomal aberrations in human lymphocytes isolated from whole blood in a dose-dependent manner.
• Uses: An isomer of the nucleoside uridine found in all species and in many classes of RNA except mRNA. It is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation. Studies suggest that β-Pseudouridine reduces radiation-induced chromosome aberrations in human lymphocytes.

Technology Process of BETA-PSEUDOURIDINE

There total 39 articles about BETA-PSEUDOURIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5'-O-(tert-butyldiphenylsilyl)-2',3'-O-(isopropylidene)pseudouridine (1024616-70-3) → pseudouridine (1445-07-4)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2007.11.039

Reference yield: 100.0%

C9H13N2O9S(1-)*Na(1+) → pseudouridine (1445-07-4)

Guidance literature:

at 70 ℃; for 2h; pH=9;

DOI:10.1021/jacs.9b08630

Reference yield: 93.0%

5-(2,3-O-isopropylidene-β-D-ribofuranosyl)uracil (28113-58-8) → pseudouridine (1445-07-4)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 5h;

DOI:10.1246/bcsj.57.2515

upstream raw materials:

(1S)-tri-O-acetyl-1-(2,4-bis-methylsulfanyl-pyrimidin-5-yl)-D-1,4-anhydro-ribitol

(1Ξ)-O²,O⁴;O³,O⁵-(R,R)-dibenzylidene-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-D-ribitol

5-(2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

5-((3S,4R,5R)-3,4-Dimethoxy-5-methoxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Downstream raw materials:

N¹-methylpseudouridine

5-(α-D-erythro-2-deoxy-pentofuranosyl)-1H-pyrimidine-2,4-dione

2'-Deoxypseudouridine

3'-Deoxy-ψ-uridine

Refernces

Synthesis of 5-fluorovinyl derivatives of pyrimidines via Suzuki-Miyaura coupling and their 1,3-dipolar cycloaddition reactions with nitrones

10.1016/j.jfluchem.2011.11.005

The research aims to develop a new class of fluorinated isoxazolidine derivatives of pyrimidine through a two-step synthesis process involving Suzuki–Miyaura coupling followed by 1,3-dipolar cycloaddition with nitrones. The purpose is to explore the synthesis of fluorinated analogues of biologically important compounds, which have unique properties relevant to medicinal chemistry and biochemistry. Key chemicals used include 5-(dihydroxyboryl)-2,4-bis(alkoxy)-pyrimidines, various fluorovinyl halides such as 1,1,2-trifluoro-2-iodoethene and perfluoroprop-1-enyl halides, and nitrones generated from paraformaldehyde and substituted hydroxylamines. The study concludes that the fluorinated isoxazolidines were successfully synthesized with complete regioselectivity and a good degree of diastereoselectivity. Mild hydrolysis conditions allowed for the removal of pyrimidine protecting groups without breaking the N–O bond of the isoxazolidine ring, leading to a fluorinated analogue of pseudouridine. The results suggest that this method provides a viable route for synthesizing fluorinated nucleoside analogues with potential applications in medicinal chemistry.