4-Thiouridine

4-Thiouridine
	source ↗
Names
	IUPAC name 4-Thiouridine
	Systematic IUPAC name 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidene-3,4-dihydropyrimidin-2(1H)-one
Identifiers
CAS Number	13957-31-8 Y;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:20480 Y;
ChemSpider	2297547 Y;
ECHA InfoCard	100.034.291
EC Number	237-735-3;
MeSH	Thiouridine
PubChem CID	3032615;
UNII	U9TYQ2R33J Y;
CompTox Dashboard (EPA)	DTXSID30930508 ;
	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 Key: ZLOIGESWDJYCTF-XVFCMESISA-N;
	SMILES C1=CN(C(=O)NC1=S)C2C(C(C(O2)CO)O)O;
Properties
Chemical formula	C9H12N2O5S
Molar mass	260.26 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Thiouridine is an atypical nucleoside formed with the 4-thiouracil base found in transfer RNA (tRNA).¹ Its biosynthesis has been determined.²

The IUPAC reserved the single-letter nucleobase code "S" for thiouridine in 1970, but the convention does not appear very common.³ "S" was repurposed to mean "C or G" in 1984.⁴

References

Alberts, Bruce (18 November 2014). Molecular biology of the cell (Sixth ed.). New York, NY. p. 337. ISBN 978-0-8153-4432-2. OCLC 887605755.{{cite book}}: CS1 maint: location missing publisher (link)
Park, Chung-Min; Weerasinghe, Laksiri; Day, Jacob J.; Fukuto, Jon M.; Xian, Ming (2015). "Persulfides: Current knowledge and challenges in chemistry and chemical biology". Molecular BioSystems. 11 (7): 1775–1785. doi:10.1039/c5mb00216h. PMC 4470748. PMID 25969163.
IUPAC-IUB Commission on Biochemical Nomenclature (1970). "Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents". Biochemistry. 9 (20): 4022–4027. doi:10.1021/bi00822a023.
Nomenclature Committee of the International Union of Biochemistry (NC-IUB) (1984). "Nomenclature for Incompletely Specified Bases in Nucleic Acid Sequences". Nucleic Acids Research. 13 (9): 3021–3030. doi:10.1093/nar/13.9.3021. PMC 341218. PMID 2582368.

[1] Alberts, Bruce (18 November 2014). Molecular biology of the cell (Sixth ed.). New York, NY. p. 337. ISBN 978-0-8153-4432-2. OCLC 887605755.{{cite book}}: CS1 maint: location missing publisher (link)

[Xian-2] Park, Chung-Min; Weerasinghe, Laksiri; Day, Jacob J.; Fukuto, Jon M.; Xian, Ming (2015). "Persulfides: Current knowledge and challenges in chemistry and chemical biology". Molecular BioSystems. 11 (7): 1775–1785. doi:10.1039/c5mb00216h. PMC 4470748. PMID 25969163.

[3] IUPAC-IUB Commission on Biochemical Nomenclature (1970). "Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents". Biochemistry. 9 (20): 4022–4027. doi:10.1021/bi00822a023.

[iupac-4] Nomenclature Committee of the International Union of Biochemistry (NC-IUB) (1984). "Nomenclature for Incompletely Specified Bases in Nucleic Acid Sequences". Nucleic Acids Research. 13 (9): 3021–3030. doi:10.1093/nar/13.9.3021. PMC 341218. PMID 2582368.

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