4-Thiouridine

4-Thiouridine

Names
Preferred 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

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.
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.
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.