2-Thiouridine

Base Information

• Chemical Name: 2-Thiouridine
• CAS No.: 20235-78-3
• Molecular Formula: C9H12N2O5S
• Molecular Weight: 260.271
• DSSTox Substance ID: DTXSID90174087
• Nikkaji Number: J151.225K
• Wikidata: Q20890502
• Metabolomics Workbench ID: 61251
• Mol file: 20235-78-3.mol

Synonyms:2-thiouridine

Chemical Property of 2-Thiouridine

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 216-218 °C
• Refractive Index: 1.732
• PKA: 6.98±0.20(Predicted)
• PSA: 139.80000
• Density: 1.72 g/cm³
• LogP: -1.48260
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Water (Slightly, Heated)
• 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:

97% ^*data from raw suppliers

2-Thiouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=S)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=S)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Uses: Modified nucleotide, essential for normal cell growth in some bacterial species. This compound is also able to chelate several metal ions.

Technology Process of 2-Thiouridine

There total 7 articles about 2-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: 38.0%

2-thiocytidine (13233-20-0,13239-97-9) → 2-thiouracil (141-90-2,156-82-1) + 2-thiocytosine (333-49-3) + 2-thiouridine (20235-78-3)

Guidance literature:

With formic acid; water; at 60 ℃; for 1296h; pH=3;

DOI:10.1038/nchem.2664

Reference yield: 33.0%

2-thiocytidine (13233-20-0,13239-97-9) → 2-thiouridine (20235-78-3) + CYTIDINE (65-46-3)

Guidance literature:

With water; In aq. phosphate buffer; at 60 ℃; for 2016h; pH=5;

DOI:10.1038/nchem.2664

Reference yield: 15.0%

5-O-(4,4-dimethoxytrityl)-2-O-tetrahydropyranyl-2-thiouridine-3-O-succinyl-NH(CH2)11-Si(OEt)2-CPG → 2-thiouridine (20235-78-3) + 1-(β-D-ribofuranosyl)-4-pyrimidinone (21052-20-0) + uridine (58-96-8)

Guidance literature:

5\-O-(4,4\-dimethoxytrityl)-2\-O-tetrahydropyranyl-2-thiouridine-3\-O-succinyl-NH(CH₂)11-Si(OEt)2-CPG; With iodine; In pyridine; water; for 0.166667h;

With trichloroacetic acid; for 0.5h;

With ammonia; In ethanol; at 20 ℃; for 18h;

DOI:10.1081/NCN-100107198

upstream raw materials:

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

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

2-thiocytidine

Downstream raw materials:

2-thiouracil

2',3'-O-isopropylidene-2-thiouridine

5-hydroxymethyl-2',3'-O-isopropylidene-2-thiouridine

5'-O-dimetoxytrityl-2-selenouridine

Refernces

• 1、 Xu, Jianfeng,Tsanakopoulou, Maria,Magnani, Christopher J.,Szabla, Rafa?,?poner, Judit E.,?poner, Ji?í,Góra, Robert W.,Sutherland, John D.. "A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization". . p. 303 - 309. Retrieved 2017/04/03.