{{Chembox | Verifiedfields = | Watchedfields = | verifiedrevid = | ImageFile = File:4-Thiouridine_Structural_Formula_V.1_1.svg | ImageSize = | IUPACName = 4-Thiouridine | SystematicName = 1-[(2''R'',3''R'',4''S'',5''R'')-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidene-3,4-dihydropyrimidin-2(1''H'')-one | OtherNames = |Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2297547 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = U9TYQ2R33J | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = | ChEBI = 20480 | ChEBI_Ref = {{ebicite|correct|EBI}} | EC_number = 237-735-3 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 13957-31-8 | PubChem = 3032615 | StdInChI=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 | StdInChIKey = ZLOIGESWDJYCTF-XVFCMESISA-N | SMILES = C1=CN(C(=O)NC1=S)C2C(C(C(O2)CO)O)O | MeSHName = Thiouridine | KEGG_Ref = | KEGG = }} |Section2 = {{Chembox Properties | C=9 | H=12 | N=2 | O=5 | S=1 | Appearance = | Density = | MeltingPtC = | MeltingPt_notes = | BoilingPt = | Solubility = }} |Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | GHSPictograms = | GHSSignalWord = | HPhrases = | PPhrases = }} }}
'''4-Thiouridine''' is an atypical nucleoside formed with the 4-thiouracil base found in transfer RNA (tRNA).<ref>{{Cite book|last=Alberts, Bruce|title=Molecular biology of the cell|date=18 November 2014|publisher=|isbn=978-0-8153-4432-2|edition=Sixth|location=New York, NY|pages=337|oclc=887605755}}</ref> Its biosynthesis has been determined.<ref name=Xian>{{cite journal |doi=10.1039/c5mb00216h|title=Persulfides: Current knowledge and challenges in chemistry and chemical biology|year=2015|last1=Park|first1=Chung-Min|last2=Weerasinghe|first2=Laksiri|last3=Day|first3=Jacob J.|last4=Fukuto|first4=Jon M.|last5=Xian|first5=Ming|journal=Molecular BioSystems|volume=11|issue=7|pages=1775–1785|pmid=25969163|pmc=4470748}}</ref>
The IUPAC reserved the single-letter nucleobase code "S" for thiouridine in 1970, but the convention does not appear very common.<ref>{{Cite journal | author = IUPAC-IUB Commission on Biochemical Nomenclature | doi = 10.1021/bi00822a023 | title = Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents | journal = Biochemistry | volume = 9 | issue = 20 | pages = 4022–4027 | year = 1970 }}</ref> "S" was repurposed to mean "C or G" in 1984.<ref name="iupac">{{cite journal|author=Nomenclature Committee of the International Union of Biochemistry (NC-IUB)|year=1984|title=Nomenclature for Incompletely Specified Bases in Nucleic Acid Sequences|journal=Nucleic Acids Research|volume=13|issue=9|pages=3021–3030|doi=10.1093/nar/13.9.3021|pmid=2582368|pmc=341218}}</ref>
== References == {{reflist}} {{DEFAULTSORT:Thiouridine}} Category:Nucleosides Category:Pyrimidines Category:Hydroxymethyl compounds
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