Sulfur-modified Nucleosides: Thiouridines

Thiouridine is one of the modified nucleosides in which the oxygen atom of uracil is replaced by a sulfur atom, forming 4-thiouridine and 2-thiouridine. 4-Thiouridine is a photoactivatable nucleoside and RNAs incorporated with 4-thiouridine are cross-linked to interacting proteins by UV light, so that it can be utilized in a kind of RNA analysis and isolation, PAR-CLIP method.¹⁾ On the other hand, 2-thiouridine is one of the sulfur-modified nucleosides found in tRNA. Since sulfur atom has a larger atomic radius and higher polarizability than oxygen atom and inhibits the formation of mismatched base pairs, the selectivity of antisense oligonucleotides and siRNAs containing 2-thiouridine is expected to be improved.²⁾

We have various 4- and 2-thiouridine derivatives (1, 2, 3, 4) as sulfur-modified nucleosides. Please contact us for further information on scale-up production or custom synthesis of sulfur-modified nucleosides not listed in our catalog.

Related Products

T4059

4-Thiouridine

D6061

2'-Deoxy-4-thiouridine

D6030

2'-Deoxy-2'-fluoro-4-thiouridine

T4108

2-Thiouridine

References

• 1) Transcriptome-wide identification of RNA-binding protein and microRNA target sites by PAR-CLIP
  • M. Hafner, M. Landthaler, L. Burger, M. Khorshid, J. Hausser, P. Berninger, A. Rothballer, M. Ascano Jr., A.-C. Jungkamp, M. Munschauer, A. Ulrich, G. S. Wardle, S. Dewell, M. Zavolan, T. Tuschl, Cell 2010, 141, 129.
• 2) Thermodynamics of RNA−RNA Duplexes with 2- or 4-Thiouridines:  Implications for Antisense Design and Targeting a Group I Intron
  • S. M. Testa, M. D. Disney, D. H. Turner, R. Kierzek, Biochemistry 1999, 38, 16655.

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