13957-31-8 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.
Check Digit Verification of cas no
The CAS Registry Mumber 13957-31-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,9,5 and 7 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13957-31:
(7*1)+(6*3)+(5*9)+(4*5)+(3*7)+(2*3)+(1*1)=118
118 % 10 = 8
So 13957-31-8 is a valid CAS Registry Number.
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)
13957-31-8Relevant 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.
Pal,Uziel,Doherty,Cohn
, p. 3634 - 3638 (1969)
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Some synthetic analogues of uridine diphosphate glucose.
Kochetkov,Budowsky,Shibaev,Yeliseeva,Grachev,Demushkin
, p. 1207 - 1218 (1963)
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Anti-hepatitis B virus compound as well as preparation method and application thereof
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, (2021/06/22)
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
Zhang, Xiaohui,Wang, Jian,Xu, Yao-Zhong
, p. 523 - 529 (2013/09/02)
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