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13957-31-8

  • Product Name:4-thiouridine
  • Molecular Formula:C9H12N2O5S
  • Purity:99%
  • Molecular Weight:260.271
Inquiry

Product Details;

CasNo: 13957-31-8

Molecular Formula: C9H12N2O5S

Appearance: Light yellow crystalline

High Quality Factory Sells 4-thiouridine 13957-31-8 In Bulk Supply

  • Molecular Formula:C9H12N2O5S
  • Molecular Weight:260.271
  • Appearance/Colour:Light yellow crystalline 
  • Melting Point:139-140℃ (ethanol ) 
  • Refractive Index:1.732 
  • PKA:4.75±0.20(Predicted) 
  • PSA:139.80000 
  • Density:1.72 g/cm3 
  • LogP:-1.48260 

4-THIOURIDINE(Cas 13957-31-8) Usage

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. 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.

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.

InChI:InChI=1/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)

13957-31-8 Relevant articles

Isolation and characterization of pyrimidine sulfenic acid via scission of the sulfur-sulfur bond in the methyl analog of bis(4-thiouridine) disulfide.

Pal,Uziel,Doherty,Cohn

, p. 3634 - 3638 (1969)

-

Chemical Conversion of Uridine into 4-Thiouridine via the 4-(1,2,4-Triazol-1-yl)pyrimidin-2(1H)-one Intermediate

Sung, Wing L.

, p. 522 - 523 (1982)

In an aqueous solution of sodium hydrosu...

Some synthetic analogues of uridine diphosphate glucose.

Kochetkov,Budowsky,Shibaev,Yeliseeva,Grachev,Demushkin

, p. 1207 - 1218 (1963)

-

Synthesis and Metabolic Fate of 4-Methylthiouridine in Bacterial tRNA

Borek, Christoph,Reichle, Valentin F.,Kellner, Stefanie

, p. 2768 - 2771 (2020)

Ribonucleic acid (RNA) is central to man...

Anti-hepatitis B virus compound as well as preparation method and application thereof

-

Paragraph 0033-0035, (2021/06/22)

The invention provides an anti-hepatitis...

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

-

, (2019/01/15)

This invention provides expressible poly...

Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides

Zhang, Xiaohui,Wang, Jian,Xu, Yao-Zhong

, p. 523 - 529 (2013/09/02)

Unambiguous characterization of 5-substi...

13957-31-8 Process route

4-thio-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-(3H)-pyrimidine-2,4-dione
55003-25-3

4-thio-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-(3H)-pyrimidine-2,4-dione

4-thiouridine
13957-31-8

4-thiouridine

Conditions
Conditions Yield
With ammonia; In methanol; for 12h;
90%
With sodium methylate;
89%
With ammonia; In methanol; at 20 ℃; for 4.5h;
With methanol; ammonia; at 20 ℃; for 16h;
uridine
58-96-8

uridine

4-thiouridine
13957-31-8

4-thiouridine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 97 percent / (Me3Si)2NH
2: 54 percent / NaH / tetrahydrofuran
3: 54 percent / K2CO3 / aq. ethanol / 3 h / 25 °C
4: AcOH / tetrahydrofuran; H2O
5: 95 percent / conc. NH4OH / 0.5 h / 25 °C
With ammonium hydroxide; sodium hydride; potassium carbonate; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; ethanol; water;
Multi-step reaction with 3 steps
1: pyridine
2: P2S5
3: methanol. sodium methylate
With pyridine; tetraphosphorus decasulfide; sodium methylate;
Multi-step reaction with 3 steps
1: pyridine / 3 h / 60 °C
2: Lawessons reagent / benzene / 24 h / Reflux
3: ammonia / methanol / 12 h
With Lawessons reagent; pyridine; ammonia; In methanol; benzene;
Multi-step reaction with 3 steps
1: pyridine / 5 h / 0 °C
2: tetraphosphorus decasulfide / 1,4-dioxane / 1.5 h / 106 °C
3: ammonia / methanol / 4.5 h / 20 °C
With pyridine; tetraphosphorus decasulfide; ammonia; In 1,4-dioxane; methanol;
Multi-step reaction with 3 steps
1: iodine / 0.75 h / 20 °C
2: tetraphosphorus decasulfide; pyridine / 4 h / Reflux
3: ammonium hydroxide / water / 2 h / Reflux
With pyridine; ammonium hydroxide; tetraphosphorus decasulfide; iodine; In water;

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