2-Thiouridine-5'-Triphosphate

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N-1032
2-Thio-UTP
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SKU Unit Size Price Qty
N-1032-1 1 µmole
$91.00
N-1032-5 5 µmole
$438.00
N-1032-10 10 µmole
$750.00
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Description

2-Thiouridine-5'-Triphosphate (2-Thio-UTP) is a substrate for several DNA polymerases and will substitute for UTP (Nakayama et al.). 2-Thio-UTP is an inhibitor of norovirus RNA dependent RNA polymerase (Belliot et al.). RNAs prepared from 2-Thio-UTP is less immunogenic as compared to unmodified RNA. 2-Thio-U modified mRNA shows no activation of RNA-dependent protein kinase (Anderson et al.), significantly reduced levels of 2'-5'-oligoadenylate synthetase activation (Anderson et al.), reduced levels of retinoic acid-inducible protein I (Hornung et al.) and suppression of activation of Toll-like receptors (Kariko et al.). However, 2-Thio-U modified mRNAs show poor translation efficiency in cell-free systems and in cultured cells (Kariko et al., Zimmer et al.). 2-Thio-UTP is a competitive inhibitor of CTP synthetase (Scheit et al.) and a potent and selective agonist of P2Y2 human receptor (El-Tayeb, et al., Jacobson et al., Ko et al., Govindan et al.).

Product Details

Catalog No N-1032
Purity ≥95% by AX-HPLC
Extinction Coefficient 13,120 Lmol-1cm-1 at 274 nm
Molecular Formula C9H15N2O14P3S (free acid)
Molecular Weight 500.20 g/mole (free acid)
Salt Form Li+
Concentration 100 mM
Buffer H2O
Recommended Storage -20°C or below
Other Name(s) 2-Thio-UTP
Application Aptamers, Epigenetics/DNA Damage, In vitro Transcription, Mutagenesis, Photocrosslinking Studies
Backbone 5'-Triphosphate
Base Analog(s) Uridine
Sugar Type(s) RNA
Nucleotide Category Base Modified RNA

Technical Documents




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References

Veres, Z.; Tsai, L.; Scholz, T. D.; Politino, M.; Balaban, R. S.; Stadtman, T. C. . Synthesis of 5-methylaminomethyl-2-selenouridine in tRNAs: 31P NMR studies show the labile selenium donor synthesized by the selD gene product contains selenium bonded to phosphorus.

Besada, Pedro; Shin, Dae Hong; Costanzi, Stefano; Ko, Hyojin; Mathé, Christophe; Gagneron, Julien; Gosselin, Gilles; Maddileti, Savitri; Harden, T. Kendall; Jacobson, Kenneth A. . Structure-Activity Relationships of Uridine 5`-Diphosphate Analogues at the Human P2Y6Receptor

Karikó, Katalin; Muramatsu, Hiromi; Welsh, Frank A.; Ludwig, János; Kato, Hiroki; Akira, Shizuo; Weissman, Drew . Incorporation of pseudouridine into mRNA yields superior nonimmunogenic vector with increased translational capacity and biological stability.

Karikó, Katalin; Buckstein, Michael; Ni, Houping; Weissman, Drew . Suppression of RNA recognition by Toll-like receptors: the impact of nucleoside modification and the evolutionary origin of RNA.

Anderson, Bart R.; Muramatsu, Hiromi; Nallagatla, Subba R.; Bevilacqua, Philip C.; Sansing, Lauren H.; Weissman, Drew; Karikó, Katalin . Incorporation of pseudouridine into mRNA enhances translation by diminishing PKR activation.

Anderson, Bart R.; Muramatsu, Hiromi; Jha, Babal K.; Silverman, Robert H.; Weissman, Drew; Karikó, Katalin . Nucleoside modifications in RNA limit activation of 2'-5'-oligoadenylate synthetase and increase resistance to cleavage by RNase L.

Hornung, Veit; Ellegast, Jana; Kim, Sarah; Brzózka, Krzysztof; Jung, Andreas; Kato, Hiroki; Poeck, Hendrik; Akira, Shizuo; Conzelmann, Karl-Klaus; Schlee, Martin; Endres, Stefan; Hartmann, Gunther . 5'-Triphosphate RNA is the ligand for RIG-I.

Govindan, Sriram; Taylor, Colin W. . P2Y receptor subtypes evoke different Ca2+ signals in cultured aortic smooth muscle cells.

Nakayama, C.; Saneyoshi, M. . Utilizations of various uridine 5'-triphosphate analogues by DNA-dependent RNA polymerases I and II purified from liver nuclei of the cherry salmon (Oncorhynchus masou).

Zimmer, M.; Scheit, K. H. . The effect of nucleotide analogs on cell-free gene expression.

Scheit, K. H.; Linke, H. J. . Substrate specificity of CTP synthetase from Escherichia coli.

Ko, Hyojin; Fricks, Ingrid; Ivanov, Andrei A.; Harden, T. Kendall; Jacobson, Kenneth A. . Structure-activity relationship of uridine 5'-diphosphoglucose analogues as agonists of the human P2Y14 receptor.

Ko, Hyojin; Carter, Rhonda L.; Cosyn, Liesbet; Petrelli, Riccardo; de Castro, Sonia; Besada, Pedro; Zhou, Yixing; Cappellacci, Loredana; Franchetti, Palmarisa; Grifantini, Mario; Van Calenbergh, Serge; Harden, T. Kendall; Jacobson, Kenneth A. . Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists.

Uchida, Satoshi; Itaka, Keiji; Uchida, Hirokuni; Hayakawa, Kentaro; Ogata, Toru; Ishii, Takehiko; Fukushima, Shigeto; Osada, Kensuke; Kataoka, Kazunori . In vivo messenger RNA introduction into the central nervous system using polyplex nanomicelle.

Baba, Miyuki; Itaka, Keiji; Kondo, Kenji; Yamasoba, Tatsuya; Kataoka, Kazunori . Treatment of neurological disorders by introducing mRNA in vivo using polyplex nanomicelles.

Uchida, Satoshi; Kataoka, Kazunori; Itaka, Keiji . Screening of mRNA Chemical Modification to Maximize Protein Expression with Reduced Immunogenicity.

Muller, Margit S.; Taylor, Colin W. . ATP evokes Ca(2+) signals in cultured foetal human cortical astrocytes entirely through G protein-coupled P2Y receptors.