2-Thiouridine

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].

Product Specifications

CAS Number

[20235-78-3]

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.