4-Thiouridine

Base Information

• Chemical Name: 4-Thiouridine
• CAS No.: 13957-31-8
• Molecular Formula: C9H12N2O5S
• Molecular Weight: 260.271
• Hs Code.: 29349990
• European Community (EC) Number: 237-735-3
• UNII: U9TYQ2R33J
• DSSTox Substance ID: DTXSID30930508
• Nikkaji Number: J216.790E
• Wikipedia: 4-Thiouridine
• Wikidata: Q20890501
• Metabolomics Workbench ID: 53762
• Mol file: 13957-31-8.mol

Synonyms:4 Thiouridine;4-Thiouridine;Thiouridine

Chemical Property of 4-Thiouridine

Chemical Property:

• Appearance/Colour: Light yellow crystalline
• Melting Point: 139-140℃ (ethanol )
• Refractive Index: 1.732
• PKA: 4.75±0.20(Predicted)
• PSA: 139.80000
• Density: 1.72 g/cm³
• LogP: -1.48260
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: Soluble in water (20 mg/ml), and methanol (10 mg/ml).
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 260.04669266
• Heavy Atom Count: 17
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

4-Thiouridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=S)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=S)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Description: 4-Thiouridine (4-SU) is a photoactivatable ribonucleoside analog that is widely used for RNA analysis, including short-range RNA-RNA crosslinking and nascent RNA labeling. The crosslinking thio moiety is attached directly to the nucleotide base, thus 4-SU differs from uridine only by a single sulfur substitution. This offers the advantage of incorporating into an RNA chain with minimal structural perturbation and with similar base-pairing properties, reducing the likelihood that substitution will impair RNA interactions or activities.
• Uses: Nucleotide analogue, essential for cell growth in certain bacterial species. This compound is also able to chelate with certain metal ions, and in tRNA it can act as a built-in antiphotomutagenic agent that protects Escherichia coli cells against mutagenesis. 4-Thiouridine is a photoreactive (crosslinking) uridine analogue that upon phosphorylation to 4-thioUTP may be incorporated into RNA structures. 4-Thiouridine may be used to study the specificity and kinetics of uridine-cytidine kinases. 4-Thiouridine is a constituent of several transfer RNA's. 4-Thiouridine is a thionucleobase used as an antisense agent. Widely used for RNA analysis including RNA-RNA cross coupling and RNA labelling. 4-Thiouridine is a photoreactive (crosslinking) uridine analogue that upon phosphorylation to 4-thioUTP may be incorporated into RNA structures. 4-Thiouridine may be used to study the specificity and kinetics of uridine-cytidine kinases. 4-Thio Uridine is typically used to modify oligos slated for RNA, or RNA-protein, structural studies. A 4-thio-rU modified RNA pentamer was used to study the effect of this modification on codon-anticodon interaction when it is in the wobble position of tRNA.

Technology Process of 4-Thiouridine

There total 25 articles about 4-Thiouridine 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: 95.0%

S-(2-cyanoethyl)-4-thiouridine (136055-18-0) → 4-thiouridine (13957-31-8)

Guidance literature:

With ammonium hydroxide; at 25 ℃; for 0.5h;

DOI:10.1016/0040-4039(91)80679-Z

Reference yield: 90.0%

4-thio-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-(3H)-pyrimidine-2,4-dione (55003-25-3) → 4-thiouridine (13957-31-8)

Guidance literature:

With ammonia; In methanol; for 12h;

DOI:10.1021/jm1016297

Reference yield: 83.0%

1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (109389-25-5) → 4-thiouridine (13957-31-8)

Guidance literature:

With hydrogen sulfide; In methanol; triethylamine; for 5h; Ambient temperature;

DOI:10.1080/07328319708002521

upstream raw materials:

1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil

2-methoxy-1-β-D-ribofuranosyl-pyrimidine-4-one

S-(2-cyanoethyl)-4-thiouridine

4-ethoxy-1-(β-D-ribofuranosyl)-2(1H)-pyrimidinone

Downstream raw materials:

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxylamino)pyrimidin-2(1H)-one

Di-(4-deoxy-4-uridinyl)-disulfid

4-thiouracil

4-Thiouridin-5'-phosphat

Refernces

• 1、 Sung, Wing L.. "Chemical Conversion of Uridine into 4-Thiouridine via the 4-(1,2,4-Triazol-1-yl)pyrimidin-2(1H)-one Intermediate". . p. 522 - 523. Retrieved 1982.
• 2、 Borek, Christoph,Reichle, Valentin F.,Kellner, Stefanie. "Synthesis and Metabolic Fate of 4-Methylthiouridine in Bacterial tRNA". . p. 2768 - 2771. Retrieved 2020.
• 3、 -. "SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS". . . Retrieved 2019/01/15.