5-Iodouridine

Base Information

• Chemical Name: 5-Iodouridine
• CAS No.: 1024-99-3
• Molecular Formula: C9H11IN2O6
• Molecular Weight: 370.101
• Hs Code.: 29349990
• European Community (EC) Number: 213-833-1
• UNII: YZK4KVC76P
• Nikkaji Number: J93.353H
• ChEMBL ID: CHEMBL3249838
• Mol file: 1024-99-3.mol

Synonyms:5-iodouridine;5-iodouridine, 125I-labeled

Chemical Property of 5-Iodouridine

Chemical Property:

• Melting Point: 205-207 °C (dec.)(lit.)
• Refractive Index: 1.748
• PKA: 7.94±0.10(Predicted)
• PSA: 124.78000
• Density: 2.27 g/cm³
• LogP: -2.24730
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water.
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 369.96618
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Iodouridine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)I
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)I
• Uses: 5-Iodouridine has shown to enhance the effect of gamma irradiation in hamster cells. It is used as catalytic agent, petrochemical additive, used in organic synthesis.

Technology Process of 5-Iodouridine

There total 15 articles about 5-Iodouridine 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%

uridine (58-96-8) → 5-iodouridine (1024-99-3)

Guidance literature:

With iodine; silver nitrate; In methanol; at 20 - 40 ℃;

DOI:10.1002/bkcs.11549

Reference yield: 98.0%

2',3',5'-tri-O-acetyl-5-iodouridine (84500-33-4,65499-40-3) → 5-iodouridine (1024-99-3)

Guidance literature:

With ammonia; In methanol; water; at 20 ℃; for 1h;

DOI:10.1080/00304948.2018.1462063

Reference yield: 58.0%

5-iodouracil (696-07-1) + 7-methylguanosine hydroiodide (81100-62-1) → 5-iodouridine (1024-99-3)

Guidance literature:

With potassium dihydrogenphosphate; E_. coli purine nucleoside phosphorylase; E_. coli uridine phosphorylase; In aq. buffer; at 20 ℃; for 20h; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.bbapap.2019.140292

upstream raw materials:

2',3',5'-tri-O-acetyl-5-iodouridine

ethanol

uridine

Tri-O-acetyluridine

Downstream raw materials:

5′-O-(4,4′-dimethyltrityl)-5-iodouridine

N-((E)-3-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)allyl)-2,2,2-trifluoroacetamide

2-(2,4-dioxo-4,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)morpholine

N-trit-U-morpholino

Refernces

• 1、 Camacho-García,Montoro-García,López-Pérez,Bilbao,Romero-Pérez,González-Rodríguez. "Synthesis and complementary self-association of novel lipophilic π-conjugated nucleoside oligomers". . p. 4506 - 4513. Retrieved 2015.
• 2、 Beasley, Samantha,Nguyen, Kim,Fazio, Michael,Spitale, Robert C.. "Protected pyrimidine nucleosides for cell-specific metabolic labeling of RNA". . p. 3912 - 3915. Retrieved 2018.
• 3、 Asakura, Jun-ichi,Robins, Morris J.. "Cerium(IV)-Mediated Halogenation at C-5 of Uracil Derivatives". . p. 4928 - 4933. Retrieved 1990.
• 4、 Englert, Daniel,Matveeva, Regina,Sunbul, Murat,Wombacher, Richard,J?schke, Andres. "Aptamer-based proximity labeling guides covalent RNA modification". . p. 3480 - 3483. Retrieved 2021.
• 5、 Meneghesso, Silvia,Vanderlinden, Evelien,Stevaert, Annelies,McGuigan, Christopher,Balzarini, Jan,Naesens, Lieve. "Synthesis and biological evaluation of pyrimidine nucleoside monophosphate prodrugs targeted against influenza virus". . p. 35 - 43. Retrieved 2012.
• 6、 -. "SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS". . . Retrieved 2019/01/15.