20235-78-3
Chemical Structure
2-Thiouridine
- CAS No.: 20235-78-3
- Formula:C9H12N2O5S
- Molecular Weight:260.27
IUPAC Name: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
InChIKey: GJTBSTBJLVYKAU-XVFCMESISA-N
SMILES: S=C(N1)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=CC1=O
Biological Activity: 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].
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2-Thiouridine | 99.92% | 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). | ||||||||||||||||||||
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References
- [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. [Content Brief]
- [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. [Content Brief]
- [3]. Larsen AT, et al. Thermodynamic insights into 2-thiouridine-enhanced RNA hybridization. Nucleic Acids Res. 2015 Sep 18;43(16):7675-87. [Content Brief]
- [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. [Content Brief]
