2-Thiouridine

• Description:

  2-Thiouridine is an orally active modified nucleobase. 2-Thiouridine stabilizes U:A base pairs and destabilizes U:G wobble base pairs. 2-Thiouridine significantly improves the efficiency and accuracy of nonenzymatic replication of mixed-sequence A/U-containing RNA templates. 2-Thiouridine exhibits antiviral activity against multiple positive-sense single-stranded RNA viruses (DENV2, ZIKV, YFV, JEV, WNV, CHIKV, human coronaviruses ([HCoV]-229E, HCoV-OC43, SARS-CoV), and MERS-CoV) [1][2][3][4].

• UNSPSC:

  12352200

• Hazard Statement:

  H302, H315, H319, H335

• Target:

  CHIKV; Dengue Virus; DNA/RNA Synthesis; Flavivirus; Nucleoside Antimetabolite/Analog; SARS-CoV

• Type:

  Biochemical Assay Reagents

• Related Pathways:

  Anti-infection; Cell Cycle/DNA Damage

• Field of Research:

  Infection

• Assay Protocol:

  https://www.medchemexpress.com/2-thiouridine.html

• Purity:

  99.76

• Solubility:

  DMSO : 50 mg/mL (ultrasonic) |H2O : 10 mg/mL (ultrasonic; warming; heat to 60°C)

• Smiles:

  S=C (N1) N ([C@@H]2O[C@H] (CO) [C@@H] (O) [C@H]2O) C=CC1=O

• Molecular Formula:

  C9H12N2O5S

• Molecular Weight:

  260.27

• Precautions:

  H302, H315, H319, H335

• References & Citations:

  [1]Heuberger BD, et al. Replacing uridine with 2-thiouridine enhances the rate and fidelity of nonenzymatic RNA primer extension. J Am Chem Soc. 2015 Feb 25;137 (7) :2769-75. |[2]Kumar RK, et al. Synthesis and studies on the effect of 2-thiouridine and 4-thiouridine on sugar conformation and RNA duplex stability. Nucleic Acids Res. 1997 Mar 15;25 (6) :1272-80.|[3]Larsen AT, et al. Thermodynamic insights into 2-thiouridine-enhanced RNA hybridization. Nucleic Acids Res. 2015 Sep 18;43 (16) :7675-87.|[4]Uemura K, et al. 2-thiouridine is a broad-spectrum antiviral nucleoside analogue against positive-strand RNA viruses. Proc Natl Acad Sci U S A. 2023 Oct 17;120 (42) :e2304139120.

• Shipping Conditions:

  Room Temperature

• Storage Conditions:

  -20°C, 3 years; 4°C, 2 years (Powder)

• Scientific Category:

  Biochemical Assay Reagents

• Clinical Information:

  No Development Reported

• CAS Number:

  20235-78-3