| Identification | More | [Name]
4-THIOURIDINE | [CAS]
13957-31-8 | [Synonyms]
4-THIOURIDINE
THIOURIDINE, 4-
thiouridine
4-thiouridineapprox.
4-Thio-D-uridine | [EINECS(EC#)]
237-735-3 | [Molecular Formula]
C9H12N2O5S | [MDL Number]
MFCD00006538 | [Molecular Weight]
260.27 | [MOL File]
13957-31-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
139-140℃ (ethanol ) | [density ]
1.72±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly, Sonicated) | [form ]
crystalline
| [pka]
4.75±0.20(Predicted) | [color ]
light yellow
| [PH]
8.2 | [biological source]
synthetic (organic) | [Water Solubility ]
Soluble in water (20 mg/ml), and methanol (10 mg/ml). | [λmax]
245，331 (pH 6.5)；316 (pH 12) | [InChI]
InChI=1S/C9H12N2O5S/c12-3-4-6(13)7(14)8(16-4)11-2-1-5(17)10-9(11)15/h1-2,4,6-8,12-14H,3H2,(H,10,15,17)/t4-,6-,7-,8-/m1/s1 | [InChIKey]
ZLOIGESWDJYCTF-XVFCMESISA-N | [SMILES]
OC[C@H]1O[C@@H](N2C=CC(=S)NC2=O)[C@H](O)[C@@H]1O | [CAS DataBase Reference]
13957-31-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
4-Thiouridine (4-SU) is a photoactivatable ribonucleoside analog that is widely used for RNA analysis, including short-range RNA-RNA crosslinking and nascent RNA labeling.1,2,3 The crosslinking thio moiety is attached directly to the nucleotide base, thus 4-SU differs from uridine only by a single sulfur substitution. This offers the advantage of incorporating into an RNA chain with minimal structural perturbation and with similar base-pairing properties, reducing the likelihood that substitution will impair RNA interactions or activities.3 | [Uses]
4-Thiouridine is a photoreactive (crosslinking) uridine analogue that upon phosphorylation to 4-thioUTP may be incorporated into RNA structures. 4-Thiouridine may be used to study the specificity and kinetics of uridine-cytidine kinases. | [Uses]
Nucleotide analogue, essential for cell growth in certain bacterial species. This compound is also able to chelate with certain metal ions, and in tRNA it can act as a built-in antiphotomutagenic agent that protects Escherichia coli cells against mutagenesis. | [Definition]
ChEBI: A thiouridine in which the oxygen replaced by sulfur is that at C-4. | [General Description]
4-Thiouridine is a photoreactive uridine analog. | [Biochem/physiol Actions]
4-Thiouridine plays a role in assessing nascent RNA synthesis. It also enhances site-specific crosslinking. 4-Thiouridine also acts as a photoaffinity probe due to its stability even while lacking specific photoactivation. It can also be incorporated into RNAs. | [storage]
Store at -20°C | [References]
[1] KASPAR BURGER. 4-thiouridine inhibits rRNA synthesis and causes a nucleolar stress response.[J]. RNA Biology, 2013, 10 10: 1623-1630. DOI: 10.4161/rna.26214
[2] GILLES THOMAS Alain F. 4-Thiouridine Triggers Both Growth Delay Induced by Near-Ultraviolet Light and Photoprotection[J]. The FEBS journal, 1980, 113 1: 67-74. DOI: 10.1111/j.1432-1033.1980.tb06140.x
[3] MICHAEL E HARRIS E L C. RNA crosslinking methods.[J]. Methods in enzymology, 2009, 468: 127-146. DOI: 10.1016/s0076-6879(09)68007-1 |
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