200,000+ products from a single source!
sales@angenechem.com
Home > Other Building Blocks > 13957-31-8
13957-31-8 | Uridine, 4-thio-
CAS No: 13957-31-8 Catalog No: AG001BAE MDL No:MFCD00006538
Product Description
Catalog Number:
AG001BAE
Chemical Name:
Uridine, 4-thio-
CAS Number:
13957-31-8
Molecular Formula:
C9H12N2O5S
Molecular Weight:
260.2670
MDL Number:
MFCD00006538
IUPAC Name:
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidenepyrimidin-2-one
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
InChI Key:
ZLOIGESWDJYCTF-XVFCMESISA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=S)[nH]c1=O
EC Number:
237-735-3
Properties
Complexity:
374
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
260.047g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
260.264g/mol
Monoisotopic Mass:
260.047g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
134A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.4
Literature
| Title | Journal |
|---|---|
| Biosynthesis of 4-thiouridine in tRNA in the methanogenic archaeon Methanococcus maripaludis. | The Journal of biological chemistry 20121026 |
| Ultrashort and progressive 4sU-tagging reveals key characteristics of RNA processing at nucleotide resolution. | Genome research 20121001 |
| 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. | Chemical communications (Cambridge, England) 20120725 |
| Crystal structures of murine norovirus-1 RNA-dependent RNA polymerase in complex with 2-thiouridine or ribavirin. | Virology 20120510 |
| Human tRNA(Lys3)(UUU) is pre-structured by natural modifications for cognate and wobble codon binding through keto-enol tautomerism. | Journal of molecular biology 20120302 |
| The 2-thiouridylase function of the human MTU1 (TRMU) enzyme is dispensable for mitochondrial translation. | Human molecular genetics 20111201 |
| 5-Fluoro-4-thiouridine phosphoramidite: new synthon for introducing photoaffinity label into oligodeoxynucleotides. | Bioorganic & medicinal chemistry 20111015 |
| NMR and UV studies of 4-thio-2'-deoxyuridine and its derivatives. | Molecules (Basel, Switzerland) 20110701 |
| Synthesis and decay of varicella zoster virus transcripts. | Journal of neurovirology 20110601 |
| The 2-thiouridine unit in the RNA strand is desulfured predominantly to 4-pyrimidinone nucleoside under in vitro oxidative stress conditions. | Chemical communications (Cambridge, England) 20110507 |
| 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. | PloS one 20110101 |
| Human mitochondrial tRNAs: biogenesis, function, structural aspects, and diseases. | Annual review of genetics 20110101 |
| Functional and structural impact of target uridine substitutions on the H/ACA ribonucleoprotein particle pseudouridine synthase. | Biochemistry 20100727 |
| A forward-genetic screen and dynamic analysis of lambda phage host-dependencies reveals an extensive interaction network and a new anti-viral strategy. | PLoS genetics 20100701 |
| [Functions and biosynthesis pathway of sulfur-modifications in tRNA]. | Seikagaku. The Journal of Japanese Biochemical Society 20100701 |
| Theoretical study on conformational preferences of ribose in 2-thiouridine--the role of the 2'OH group. | Physical chemistry chemical physics : PCCP 20100421 |
| Photoinduced fluorescent cross-linking of 5-chloro- and 5-fluoro-4-thiouridines with thymidine. | The Journal of organic chemistry 20100205 |
| 5-Nitro-2-pyridyl-1-thioglucosides: application in synthesis of analogues of glycosyltransferases natural substrates. | Acta poloniae pharmaceutica 20100101 |
| Chemical synthesis of LNA-2-thiouridine and its influence on stability and selectivity of oligonucleotide binding to RNA. | Biochemistry 20091124 |
| A direct synthetic approach to uracil anhydrothionucleoside derivatives. | Carbohydrate research 20091123 |
| Activity of siRNAs with 2-thio-2'-O-methyluridine modification in mammalian cells. | Nucleosides, nucleotides & nucleic acids 20091001 |
| Preparation of short interfering RNA containing the modified nucleosides 2-thiouridine, pseudouridine, or dihydrouridine. | Current protocols in nucleic acid chemistry 20090601 |
| Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine. | The Journal of organic chemistry 20090320 |
| 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. | Biochimica et biophysica acta 20090301 |
| 4-thiouridine induces dose-dependent reduction of oedema, leucocyte influx and tumour necrosis factor in lung inflammation. | Clinical and experimental immunology 20090201 |
| Common thiolation mechanism in the biosynthesis of tRNA thiouridine and sulphur-containing cofactors. | The EMBO journal 20081217 |
| A genome-wide screen identifies genes required for formation of the wobble nucleoside 5-methoxycarbonylmethyl-2-thiouridine in Saccharomyces cerevisiae. | RNA (New York, N.Y.) 20081001 |
| A study of binding features between exportin-t and Thermus thermophilus tRNA(Phe) using a photo-cross-linking method. | Biochemistry 20080826 |
| Direct evidence that ThiI is an ATP pyrophosphatase for the adenylation of uridine in 4-thiouridine biosynthesis. | Chembiochem : a European journal of chemical biology 20080811 |
| Ribosomal position and contacts of mRNA in eukaryotic translation initiation complexes. | The EMBO journal 20080604 |
| Sequence-structure-function analysis of the bifunctional enzyme MnmC that catalyses the last two steps in the biosynthesis of hypermodified nucleoside mnm5s2U in tRNA. | Proteins 20080601 |
| 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. | Bioorganic & medicinal chemistry 20080601 |
| An embarrassment of riches: the enzymology of RNA modification. | Current opinion in chemical biology 20080401 |
| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | Chemical research in toxicology 20080401 |
| Photochemical reactions of 4-thiouridine disulfide and 4-benzylthiouridine--the involvement of the 4-pyrimidinylthiyl radical. | Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080201 |
| [The environment of tRNA 3'-terminus in 80S ribosome A and P sites]. | Bioorganicheskaia khimiia 20080101 |
| Incorporation of 3'-S-phosphorothiolates into RNA: potential applications in RNAi. | Nucleic acids symposium series (2004) 20080101 |
| Chemical synthesis of RNA including 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine. | Nucleic acids symposium series (2004) 20080101 |
| Extent of metal ion-sulfur binding in complexes of thiouracil nucleosides and nucleotides in aqueous solution. | Journal of inorganic biochemistry 20070401 |
| Specificity of phage display selected peptides for modified anticodon stem and loop domains of tRNA. | The protein journal 20070101 |
| Direct evidence for enzyme persulfide and disulfide intermediates during 4-thiouridine biosynthesis. | Chemical communications (Cambridge, England) 20060807 |
| Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine. | Bioorganic & medicinal chemistry letters 20060615 |
| Orchestrating sulfur incorporation into RNA. | Nature chemical biology 20060401 |
| Specific functional interactions of nucleotides at key -3 and +4 positions flanking the initiation codon with components of the mammalian 48S translation initiation complex. | Genes & development 20060301 |
| Structural basis for sulfur relay to RNA mediated by heterohexameric TusBCD complex. | Structure (London, England : 1993) 20060201 |
| Temperature-dependent biosynthesis of 2-thioribothymidine of Thermus thermophilus tRNA. | The Journal of biological chemistry 20060127 |
| Facilitating RNA structure prediction with microarrays. | Biochemistry 20060117 |
| Mechanistic insights into sulfur relay by multiple sulfur mediators involved in thiouridine biosynthesis at tRNA wobble positions. | Molecular cell 20060106 |
| Antiproliferative effect of 4-thiouridylate on OCM-1 uveal melanoma cells. | European journal of ophthalmology 20060101 |
| A single active-site region for a group II intron. | Nature structural & molecular biology 20050701 |
| 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. | Biochemistry 20050607 |
| 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. | Organic & biomolecular chemistry 20050507 |
| Photocrosslinking detects a compact, active structure of the hammerhead ribozyme. | Biochemistry 20050322 |
| 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. | Biochemistry 20050215 |
| Generation of thiyl radicals by the photolysis of 5-iodo-4-thiouridine. | The Journal of organic chemistry 20050204 |
| SNPs analysis by use of oligonucleotides containing 2'-O-methyl-2-thiouridines. | Nucleic acids symposium series (2004) 20050101 |
| Synthesis and properties of 2'-O-methyl-4'-thioRNA. | Nucleic acids symposium series (2004) 20050101 |
| Effects of uridine, isomatitol and 4-thiouridine on in vitro cell adhesion and in vivo effects of 4-thiouridine in a lung inflammation model. | International immunopharmacology 20040901 |
| Identification of a bifunctional enzyme MnmC involved in the biosynthesis of a hypermodified uridine in the wobble position of tRNA. | RNA (New York, N.Y.) 20040801 |
| Pattern of 4-thiouridine-induced cross-linking in 16S ribosomal RNA in the Escherichia coli 30S subunit. | Biochemistry 20040720 |
| Measurement of large distances in biomolecules using double-quantum filtered refocused electron spin-echoes. | Journal of the American Chemical Society 20040630 |
| Efficient synthesis of 2',3'-dideoxy-2'-amino-3'-thiouridine. | Organic letters 20040624 |
| Recruitment of divalent metal ions by incorporation of 4-thio-2'-deoxythymidine or 4-thio-2'-deoxyuridine into DNA. | Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20040601 |
| Substrate specificity for 4-thiouridine modification in Escherichia coli. | The Journal of biological chemistry 20040528 |
| Yeast Nfs1p is involved in thio-modification of both mitochondrial and cytoplasmic tRNAs. | The Journal of biological chemistry 20040326 |
| Crystallization and preliminary X-ray crystallographic studies of the small form of glucose-inhibited division protein A from Thermus thermophilus HB8. | Acta crystallographica. Section D, Biological crystallography 20040301 |
| 4-Thio-5-bromo-2'-deoxyuridine: chemical synthesis and therapeutic potential of UVA-induced DNA damage. | Bioorganic & medicinal chemistry letters 20040223 |
| Role of low-molecular-weight substrates in functional binding of the tRNAPhe acceptor end by phenylalanyl-tRNA synthetase. | Biochemistry. Biokhimiia 20040201 |
| Effect of nucleotide replacements in tRNAPhe on positioning of the acceptor end in the complex with phenylalanyl-tRNA synthetase. | Biochemistry. Biokhimiia 20040201 |
| [Using of 4-thiouridine and 4-thiothymidine for pyrimidine nucleoside phosphorylase studing]. | Molekuliarnaia biologiia 20040101 |
| Synthesis of oligoribonucleotides containing 4-thiouridine using the convertible nucleoside approach and the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl group. | Nucleosides, nucleotides & nucleic acids 20040101 |
| 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. | The Journal of organic chemistry 20031226 |
| Prokaryotic and eukaryotic tetrameric phenylalanyl-tRNA synthetases display conservation of the binding mode of the tRNA(Phe) CCA end. | Biochemistry 20030916 |
| Monitoring RNA base structure and dynamics using site-directed spin labeling. | Biochemistry 20030610 |
| Thiation of 2'-deoxy-5,6-dihydropyrimidine nucleosides with Lawesson's reagent: characterisation of oxathiaphosphepane intermediates. | Chemical communications (Cambridge, England) 20030321 |
| MnmA and IscS are required for in vitro 2-thiouridine biosynthesis in Escherichia coli. | Biochemistry 20030204 |
| Coordination of thiouridine monophosphates with selected metal ions. | Journal of inorganic biochemistry 20030115 |
| Kinetics and mechanism for platination of thione-containing nucleotides and oligonucleotides: evaluation of the salt dependence. | Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20030101 |
| Synthesis and properties of 2'-O-alkylated 2-thiouridine derivatives and oligonucleotides containing 2'-O-alkylated 2-thiouridine derivatives. | Nucleic acids research. Supplement (2001) 20030101 |
| An RNA complex of the HIV-1 A-loop and tRNA(Lys,3) is stabilized by nucleoside modifications. | Journal of the American Chemical Society 20021204 |
| A paradigm for biological sulfur transfers via persulfide groups: a persulfide-disulfide-thiol cycle in 4-thiouridine biosynthesis. | Chemical communications (Cambridge, England) 20021121 |
| Conserved bases in the TPsi C loop of tRNA are determinants for thermophile-specific 2-thiouridylation at position 54. | The Journal of biological chemistry 20021018 |
| 4-thio-U cross-linking identifies the active site of the VS ribozyme. | The EMBO journal 20020902 |
| Identification of active antiviral compounds against a New York isolate of West Nile virus. | Antiviral research 20020701 |
| Ribosomal proteins mediate the hepatitis C virus IRES-HeLa 40S interaction. | RNA (New York, N.Y.) 20020701 |
| Accurate translation of the genetic code depends on tRNA modified nucleosides. | The Journal of biological chemistry 20020510 |
| Crosslinking of 4.5S RNA to the Escherichia coli ribosome in the presence or absence of the protein Ffh. | RNA (New York, N.Y.) 20020501 |
| Transient reduction in the tRNA 4-thiouridine content induced by ultraviolet A during post-irradiation growth in Enterobacter cloacae. | Journal of photochemistry and photobiology. B, Biology 20020401 |
| Pyrimidinethione nucleosides and their deaza analogues. | Nucleosides, nucleotides & nucleic acids 20020101 |
| The role of the cysteine residues of ThiI in the generation of 4-thiouridine in tRNA. | The Journal of biological chemistry 20010907 |
| Wobble modification defect in tRNA disturbs codon-anticodon interaction in a mitochondrial disease. | The EMBO journal 20010903 |
| Translational misreading: a tRNA modification counteracts a +2 ribosomal frameshift. | Genes & development 20010901 |
| Synthesis and hypnotic activities of 4-thio analogues of N3-substituted uridines. | Chemical & pharmaceutical bulletin 20010901 |
| Photoactivation of DNA thiobases as a potential novel therapeutic option. | Current biology : CB 20010724 |
| Determination of tRNA(Phe) nucleotides contacting the subunits of Thermus thermophilus phenylalanyl-tRNA synthetase by photoaffinity crosslinking. | Biochimica et biophysica acta 20010416 |
| THUMP--a predicted RNA-binding domain shared by 4-thiouridine, pseudouridine synthases and RNA methylases. | Trends in biochemical sciences 20010401 |
| Mutation of Gln125 to Asn selectively abolishes the thymidylate kinase activity of herpes simplex virus type 1 thymidine kinase. | Molecular pharmacology 20010201 |
| Arrangement of the central pseudoknot region of 16S rRNA in the 30S ribosomal subunit determined by site-directed 4-thiouridine crosslinking. | RNA (New York, N.Y.) 20010101 |
| Efficient assessment of modified nucleoside stability under conditions of automated oligonucleotide synthesis: characterization of the oxidation and oxidative desulfurization of 2-thiouridine. | Nucleosides, nucleotides & nucleic acids 20010101 |
| Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes. | The Biochemical journal 20001015 |
Related Products
Featured Products
© 2019 Angene International Limited. All rights Reserved.