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13957-31-8,MFCD00006538
Catalog No.:AA001B7M

13957-31-8 | 4-Thiouridine

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100mg
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250mg
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5g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001B7M
Chemical Name:
4-Thiouridine
CAS Number:
13957-31-8
Molecular Formula:
C9H12N2O5S
Molecular Weight:
260.2670
MDL Number:
MFCD00006538
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=S)[nH]c1=O
Properties
Computed Properties
 
Complexity:
374  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-1.4  

Downstream Synthesis Route

[1]JournaloftheAmericanChemicalSociety,1959,vol.81,p.178,187

[1]JournaloftheAmericanChemicalSociety,1959,vol.81,p.178,187

[1]JournaloftheAmericanChemicalSociety,1959,vol.81,p.178,187

[1]JournaloftheAmericanChemicalSociety,1992,vol.114,p.9229-9230

[1]Chemicalandpharmaceuticalbulletin,1980,vol.28,p.157-162

Literature

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Title: Ultrashort and progressive 4sU-tagging reveals key characteristics of RNA processing at nucleotide resolution.

Journal: Genome research 20121001

Title: Prediction of the stability of modified RNA duplexes based on deformability analysis: oligoribonucleotide derivatives modified with 2'-O-cyanoethyl-5-propynyl-2-thiouridine as a promising component.

Journal: Chemical communications (Cambridge, England) 20120725

Title: Crystal structures of murine norovirus-1 RNA-dependent RNA polymerase in complex with 2-thiouridine or ribavirin.

Journal: Virology 20120510

Title: Human tRNA(Lys3)(UUU) is pre-structured by natural modifications for cognate and wobble codon binding through keto-enol tautomerism.

Journal: Journal of molecular biology 20120302

Title: The 2-thiouridylase function of the human MTU1 (TRMU) enzyme is dispensable for mitochondrial translation.

Journal: Human molecular genetics 20111201

Title: 5-Fluoro-4-thiouridine phosphoramidite: new synthon for introducing photoaffinity label into oligodeoxynucleotides.

Journal: Bioorganic & medicinal chemistry 20111015

Title: NMR and UV studies of 4-thio-2'-deoxyuridine and its derivatives.

Journal: Molecules (Basel, Switzerland) 20110701

Title: Synthesis and decay of varicella zoster virus transcripts.

Journal: Journal of neurovirology 20110601

Title: The 2-thiouridine unit in the RNA strand is desulfured predominantly to 4-pyrimidinone nucleoside under in vitro oxidative stress conditions.

Journal: Chemical communications (Cambridge, England) 20110507

Title: Unexpected accumulation of ncm(5)U and ncm(5)S(2) (U) in a trm9 mutant suggests an additional step in the synthesis of mcm(5)U and mcm(5)S(2)U.

Journal: PloS one 20110101

Title: Human mitochondrial tRNAs: biogenesis, function, structural aspects, and diseases.

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Title: Functional and structural impact of target uridine substitutions on the H/ACA ribonucleoprotein particle pseudouridine synthase.

Journal: Biochemistry 20100727

Title: A forward-genetic screen and dynamic analysis of lambda phage host-dependencies reveals an extensive interaction network and a new anti-viral strategy.

Journal: PLoS genetics 20100701

Title: [Functions and biosynthesis pathway of sulfur-modifications in tRNA].

Journal: Seikagaku. The Journal of Japanese Biochemical Society 20100701

Title: Theoretical study on conformational preferences of ribose in 2-thiouridine--the role of the 2'OH group.

Journal: Physical chemistry chemical physics : PCCP 20100421

Title: Photoinduced fluorescent cross-linking of 5-chloro- and 5-fluoro-4-thiouridines with thymidine.

Journal: The Journal of organic chemistry 20100205

Title: 5-Nitro-2-pyridyl-1-thioglucosides: application in synthesis of analogues of glycosyltransferases natural substrates.

Journal: Acta poloniae pharmaceutica 20100101

Title: Chemical synthesis of LNA-2-thiouridine and its influence on stability and selectivity of oligonucleotide binding to RNA.

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Title: A direct synthetic approach to uracil anhydrothionucleoside derivatives.

Journal: Carbohydrate research 20091123

Title: Activity of siRNAs with 2-thio-2'-O-methyluridine modification in mammalian cells.

Journal: Nucleosides, nucleotides & nucleic acids 20091001

Title: Preparation of short interfering RNA containing the modified nucleosides 2-thiouridine, pseudouridine, or dihydrouridine.

Journal: Current protocols in nucleic acid chemistry 20090601

Title: Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine.

Journal: The Journal of organic chemistry 20090320

Title: Sites of 18S rRNA contacting mRNA 3' and 5' of the P site codon in human ribosome: a cross-linking study with mRNAs carrying 4-thiouridines at specific positions.

Journal: Biochimica et biophysica acta 20090301

Title: 4-thiouridine induces dose-dependent reduction of oedema, leucocyte influx and tumour necrosis factor in lung inflammation.

Journal: Clinical and experimental immunology 20090201

Title: Common thiolation mechanism in the biosynthesis of tRNA thiouridine and sulphur-containing cofactors.

Journal: The EMBO journal 20081217

Title: A genome-wide screen identifies genes required for formation of the wobble nucleoside 5-methoxycarbonylmethyl-2-thiouridine in Saccharomyces cerevisiae.

Journal: RNA (New York, N.Y.) 20081001

Title: A study of binding features between exportin-t and Thermus thermophilus tRNA(Phe) using a photo-cross-linking method.

Journal: Biochemistry 20080826

Title: Direct evidence that ThiI is an ATP pyrophosphatase for the adenylation of uridine in 4-thiouridine biosynthesis.

Journal: Chembiochem : a European journal of chemical biology 20080811

Title: Ribosomal position and contacts of mRNA in eukaryotic translation initiation complexes.

Journal: The EMBO journal 20080604

Title: Sequence-structure-function analysis of the bifunctional enzyme MnmC that catalyses the last two steps in the biosynthesis of hypermodified nucleoside mnm5s2U in tRNA.

Journal: Proteins 20080601

Title: Study of the base discrimination ability of DNA and 2'-O-methylated RNA oligomers containing 2-thiouracil bases towards complementary RNA or DNA strands and their application to single base mismatch detection.

Journal: Bioorganic & medicinal chemistry 20080601

Title: An embarrassment of riches: the enzymology of RNA modification.

Journal: Current opinion in chemical biology 20080401

Title: Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.

Journal: Chemical research in toxicology 20080401

Title: Photochemical reactions of 4-thiouridine disulfide and 4-benzylthiouridine--the involvement of the 4-pyrimidinylthiyl radical.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080201

Title: [The environment of tRNA 3'-terminus in 80S ribosome A and P sites].

Journal: Bioorganicheskaia khimiia 20080101

Title: Incorporation of 3'-S-phosphorothiolates into RNA: potential applications in RNAi.

Journal: Nucleic acids symposium series (2004) 20080101

Title: Chemical synthesis of RNA including 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine.

Journal: Nucleic acids symposium series (2004) 20080101

Title: Extent of metal ion-sulfur binding in complexes of thiouracil nucleosides and nucleotides in aqueous solution.

Journal: Journal of inorganic biochemistry 20070401

Title: Specificity of phage display selected peptides for modified anticodon stem and loop domains of tRNA.

Journal: The protein journal 20070101

Title: Direct evidence for enzyme persulfide and disulfide intermediates during 4-thiouridine biosynthesis.

Journal: Chemical communications (Cambridge, England) 20060807

Title: Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine.

Journal: Bioorganic & medicinal chemistry letters 20060615

Title: Orchestrating sulfur incorporation into RNA.

Journal: Nature chemical biology 20060401

Title: Specific functional interactions of nucleotides at key -3 and +4 positions flanking the initiation codon with components of the mammalian 48S translation initiation complex.

Journal: Genes & development 20060301

Title: Structural basis for sulfur relay to RNA mediated by heterohexameric TusBCD complex.

Journal: Structure (London, England : 1993) 20060201

Title: Temperature-dependent biosynthesis of 2-thioribothymidine of Thermus thermophilus tRNA.

Journal: The Journal of biological chemistry 20060127

Title: Facilitating RNA structure prediction with microarrays.

Journal: Biochemistry 20060117

Title: Mechanistic insights into sulfur relay by multiple sulfur mediators involved in thiouridine biosynthesis at tRNA wobble positions.

Journal: Molecular cell 20060106

Title: Antiproliferative effect of 4-thiouridylate on OCM-1 uveal melanoma cells.

Journal: European journal of ophthalmology 20060101

Title: A single active-site region for a group II intron.

Journal: Nature structural & molecular biology 20050701

Title: Structural effects of hypermodified nucleosides in the Escherichia coli and human tRNALys anticodon loop: the effect of nucleosides s2U, mcm5U, mcm5s2U, mnm5s2U, t6A, and ms2t6A.

Journal: Biochemistry 20050607

Title: beta-Selective synthesis of 2'-deoxy-5,6-dihydro-4-thiouridine, a precursor of the unstable nucleoside product of ionising radiation damage 2'-deoxy-5,6-dihydrocytidine.

Journal: Organic & biomolecular chemistry 20050507

Title: Photocrosslinking detects a compact, active structure of the hammerhead ribozyme.

Journal: Biochemistry 20050322

Title: The first position of a codon placed in the A site of the human 80S ribosome contacts nucleotide C1696 of the 18S rRNA as well as proteins S2, S3, S3a, S30, and S15.

Journal: Biochemistry 20050215

Title: Generation of thiyl radicals by the photolysis of 5-iodo-4-thiouridine.

Journal: The Journal of organic chemistry 20050204

Title: SNPs analysis by use of oligonucleotides containing 2'-O-methyl-2-thiouridines.

Journal: Nucleic acids symposium series (2004) 20050101

Title: Synthesis and properties of 2'-O-methyl-4'-thioRNA.

Journal: Nucleic acids symposium series (2004) 20050101

Title: Effects of uridine, isomatitol and 4-thiouridine on in vitro cell adhesion and in vivo effects of 4-thiouridine in a lung inflammation model.

Journal: International immunopharmacology 20040901

Title: Identification of a bifunctional enzyme MnmC involved in the biosynthesis of a hypermodified uridine in the wobble position of tRNA.

Journal: RNA (New York, N.Y.) 20040801

Title: Pattern of 4-thiouridine-induced cross-linking in 16S ribosomal RNA in the Escherichia coli 30S subunit.

Journal: Biochemistry 20040720

Title: Measurement of large distances in biomolecules using double-quantum filtered refocused electron spin-echoes.

Journal: Journal of the American Chemical Society 20040630

Title: Efficient synthesis of 2',3'-dideoxy-2'-amino-3'-thiouridine.

Journal: Organic letters 20040624

Title: Recruitment of divalent metal ions by incorporation of 4-thio-2'-deoxythymidine or 4-thio-2'-deoxyuridine into DNA.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20040601

Title: Substrate specificity for 4-thiouridine modification in Escherichia coli.

Journal: The Journal of biological chemistry 20040528

Title: Yeast Nfs1p is involved in thio-modification of both mitochondrial and cytoplasmic tRNAs.

Journal: The Journal of biological chemistry 20040326

Title: Crystallization and preliminary X-ray crystallographic studies of the small form of glucose-inhibited division protein A from Thermus thermophilus HB8.

Journal: Acta crystallographica. Section D, Biological crystallography 20040301

Title: 4-Thio-5-bromo-2'-deoxyuridine: chemical synthesis and therapeutic potential of UVA-induced DNA damage.

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Title: Role of low-molecular-weight substrates in functional binding of the tRNAPhe acceptor end by phenylalanyl-tRNA synthetase.

Journal: Biochemistry. Biokhimiia 20040201

Title: Effect of nucleotide replacements in tRNAPhe on positioning of the acceptor end in the complex with phenylalanyl-tRNA synthetase.

Journal: Biochemistry. Biokhimiia 20040201

Title: [Using of 4-thiouridine and 4-thiothymidine for pyrimidine nucleoside phosphorylase studing].

Journal: Molekuliarnaia biologiia 20040101

Title: Synthesis of oligoribonucleotides containing 4-thiouridine using the convertible nucleoside approach and the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl group.

Journal: Nucleosides, nucleotides & nucleic acids 20040101

Title: A new route to 2'-O-alkyl-2-thiouridine derivatives via 4-O-protection of the uracil base and hybridization properties of oligonucleotides incorporating these modified nucleoside derivatives.

Journal: The Journal of organic chemistry 20031226

Title: Prokaryotic and eukaryotic tetrameric phenylalanyl-tRNA synthetases display conservation of the binding mode of the tRNA(Phe) CCA end.

Journal: Biochemistry 20030916

Title: Monitoring RNA base structure and dynamics using site-directed spin labeling.

Journal: Biochemistry 20030610

Title: Thiation of 2'-deoxy-5,6-dihydropyrimidine nucleosides with Lawesson's reagent: characterisation of oxathiaphosphepane intermediates.

Journal: Chemical communications (Cambridge, England) 20030321

Title: MnmA and IscS are required for in vitro 2-thiouridine biosynthesis in Escherichia coli.

Journal: Biochemistry 20030204

Title: Coordination of thiouridine monophosphates with selected metal ions.

Journal: Journal of inorganic biochemistry 20030115

Title: Kinetics and mechanism for platination of thione-containing nucleotides and oligonucleotides: evaluation of the salt dependence.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20030101

Title: Synthesis and properties of 2'-O-alkylated 2-thiouridine derivatives and oligonucleotides containing 2'-O-alkylated 2-thiouridine derivatives.

Journal: Nucleic acids research. Supplement (2001) 20030101

Title: An RNA complex of the HIV-1 A-loop and tRNA(Lys,3) is stabilized by nucleoside modifications.

Journal: Journal of the American Chemical Society 20021204

Title: A paradigm for biological sulfur transfers via persulfide groups: a persulfide-disulfide-thiol cycle in 4-thiouridine biosynthesis.

Journal: Chemical communications (Cambridge, England) 20021121

Title: Conserved bases in the TPsi C loop of tRNA are determinants for thermophile-specific 2-thiouridylation at position 54.

Journal: The Journal of biological chemistry 20021018

Title: 4-thio-U cross-linking identifies the active site of the VS ribozyme.

Journal: The EMBO journal 20020902

Title: Identification of active antiviral compounds against a New York isolate of West Nile virus.

Journal: Antiviral research 20020701

Title: Ribosomal proteins mediate the hepatitis C virus IRES-HeLa 40S interaction.

Journal: RNA (New York, N.Y.) 20020701

Title: Accurate translation of the genetic code depends on tRNA modified nucleosides.

Journal: The Journal of biological chemistry 20020510

Title: Crosslinking of 4.5S RNA to the Escherichia coli ribosome in the presence or absence of the protein Ffh.

Journal: RNA (New York, N.Y.) 20020501

Title: Transient reduction in the tRNA 4-thiouridine content induced by ultraviolet A during post-irradiation growth in Enterobacter cloacae.

Journal: Journal of photochemistry and photobiology. B, Biology 20020401

Title: Pyrimidinethione nucleosides and their deaza analogues.

Journal: Nucleosides, nucleotides & nucleic acids 20020101

Title: The role of the cysteine residues of ThiI in the generation of 4-thiouridine in tRNA.

Journal: The Journal of biological chemistry 20010907

Title: Wobble modification defect in tRNA disturbs codon-anticodon interaction in a mitochondrial disease.

Journal: The EMBO journal 20010903

Title: Translational misreading: a tRNA modification counteracts a +2 ribosomal frameshift.

Journal: Genes & development 20010901

Title: Synthesis and hypnotic activities of 4-thio analogues of N3-substituted uridines.

Journal: Chemical & pharmaceutical bulletin 20010901

Title: Photoactivation of DNA thiobases as a potential novel therapeutic option.

Journal: Current biology : CB 20010724

Title: Determination of tRNA(Phe) nucleotides contacting the subunits of Thermus thermophilus phenylalanyl-tRNA synthetase by photoaffinity crosslinking.

Journal: Biochimica et biophysica acta 20010416

Title: THUMP--a predicted RNA-binding domain shared by 4-thiouridine, pseudouridine synthases and RNA methylases.

Journal: Trends in biochemical sciences 20010401

Title: Mutation of Gln125 to Asn selectively abolishes the thymidylate kinase activity of herpes simplex virus type 1 thymidine kinase.

Journal: Molecular pharmacology 20010201

Title: Arrangement of the central pseudoknot region of 16S rRNA in the 30S ribosomal subunit determined by site-directed 4-thiouridine crosslinking.

Journal: RNA (New York, N.Y.) 20010101

Title: Efficient assessment of modified nucleoside stability under conditions of automated oligonucleotide synthesis: characterization of the oxidation and oxidative desulfurization of 2-thiouridine.

Journal: Nucleosides, nucleotides & nucleic acids 20010101

Title: Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes.

Journal: The Biochemical journal 20001015

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Tags:13957-31-8 Molecular Formula|13957-31-8 MDL|13957-31-8 SMILES|13957-31-8 4-Thiouridine