13957-31-8

Basic information

• Product Name: 4-THIOURIDINE
• Synonyms: 1-((2R,3R,4S,5R);-4-thioxo-3,4-dihydropyrimidin-2(1H);THIOURIDINE, 4-;4-THIOURIDINE;thiouridine;4-thiouridineapprox.;4-Thio-D-uridine;4-SH-Ur
• CAS NO: 13957-31-8
• Molecular Formula: C₉H₁₂N₂O₅S
• Molecular Weight: 260.27
• EINECS: 237-735-3
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides;Bases & Related Reagents;Nucleotides;Sulfur & Selenium Compounds
• Mol File: 13957-31-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 139-140℃ (ethanol )
• Appearance: light yellow/crystalline
• Density: 1.72 g/cm³
• Refractive Index: 1.732
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 4.75±0.20(Predicted)
• Water Solubility: Soluble in water (20 mg/ml), and methanol (10 mg/ml).
• CAS DataBase Reference: 4-THIOURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-THIOURIDINE(13957-31-8)
• EPA Substance Registry System: 4-THIOURIDINE(13957-31-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 13957-31-8(Hazardous Substances Data)

Usage

Description

4-Thiouridine (4-SU) is a photoreactive uridine analog that is widely used for RNA analysis, including short-range RNA-RNA crosslinking and nascent RNA labeling. It is a thionucleobase used as an antisense agent and is a constituent of several transfer RNAs. The crosslinking thio moiety is attached directly to the nucleotide base, differing 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

Used in Bacterial Cell Growth:
4-Thiouridine is used as a nucleotide analog for cell growth in certain bacterial species, such as Escherichia coli. It can act as a built-in antiphotomutagenic agent that protects these cells against mutagenesis.
Used in RNA Analysis:
4-Thiouridine is used as a photoreactive (crosslinking) uridine analogue that, upon phosphorylation to 4-thioUTP, may be incorporated into RNA structures. It is used to study the specificity and kinetics of uridine-cytidine kinases and is widely used for RNA analysis, including RNA-RNA cross coupling and RNA labeling.
Used in RNA-Protein Structural Studies:
4-Thiouridine is used to modify oligos slated for RNA or RNA-protein structural studies. A 4-thio-rU modified RNA pentamer was used to study the effect of this modification on codon-anticodon interaction when it is in the wobble position of tRNA.
Used in Chelation of Metal Ions:
4-Thiouridine is also able to chelate with certain metal ions, making it useful in various applications where metal ion binding is required.

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)

Upstream product

• 15049-50-0 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil 
• 53337-88-5 2-methoxy-1-β-D-ribofuranosyl-pyrimidine-4-one 
• 59495-20-4 4-ethoxy-1-(β-D-ribofuranosyl)-2(1H)-pyrimidinone 
• 6773-44-0 5'-acetyluridine 
• 22249-19-0 O^5'-acetyl-4-thio-uridine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 55003-25-3 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-mercapto-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 4105-38-8 Tri-O-acetyluridine 
• 58-96-8 uridine 
• 82913-19-7 [(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate 
• 1748-04-5 tribenzoyl uridine 
• 10457-16-6 2',3',5,-tris-O-(trimethylsilyl)uridine 
• 136055-16-8 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester 
• 136055-17-9 3-[1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylsulfanyl]-propionitrile 

Downstream Products

• 31556-28-2 4-thiouridine 5'-triphosphate 
• 591-28-6 4-thiouracil 
• 4145-46-4 4-Thiouridin-5'-phosphat 
• 73719-83-2 1-β-D-ribofuranosyl-4-phenacylidene-2-(3H)-pyrimidone 
• 219709-47-4 4-S-pivaloyloxymethyl-5'-O-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-4-thiouridine 
• 219709-48-5 4-S-pivaloyloxymethyl-2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-4-thiouridine 
• 136671-59-5 5'-O-dimethoxytrityl-4-thiouridine 
• 18427-02-6 Di-(4-deoxy-4-uridinyl)-disulfid 
• 58-96-8 uridine 
• 73719-79-6 4-phenacylthiouridine 
• 74972-87-5 S-(N-(4-anilino-1-naphthyl)carbamylmethyl)-4-thiouridine 
• 144303-79-7 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-methyldisulfanyl-1H-pyrimidin-2-one 
• 3258-02-4 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxylamino)pyrimidin-2(1H)-one 

Relevant articles and documents

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

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Some synthetic analogues of uridine diphosphate glucose.

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

The invention provides an anti-hepatitis B virus compound and a preparation method and application thereof, the compound is 4-thiouridine isobutyrate, the molecular formula is C13H18N2O6S, and the structural formula is shown in the specification. The compound provided by the invention can effectively inhibit the activity of hepatitis B virus, can be used as a substitute drug for lamivudine and telbivudine, solves the problem of drug resistance of lamivudine and the like in the aspect of resisting hepatitis B virus, is high in drug effect, low in toxicity and low in price, and provides a direction for development of drugs for treating hepatitis B. In addition, the invention discloses a preparation method of the compound 4-thiouridine isobutyrate, and the preparation method is mild in condition, easy to synthesize and suitable for industrial production.

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

Unambiguous characterization of 5-substituted-4-thiopyrimidine nucleosides (ribonucleosides and 2'-deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5-bromo-4-thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4-thiopyrimidine nucleosides are compared, and the key contributing factors discussed. The approach presented here is applicable to other modified nucleosides and nucleotides, as well as nucleobases. Copyright