5-Methyluridine

5-Methyluridine
Names
	IUPAC name 5-Methyluridine
	Systematic IUPAC name 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
	Other names Ribothymidine, Ribosylthymine; Thymine riboside, m5U
Identifiers
CAS Number	1463-10-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	393058 ;
ECHA InfoCard	100.014.522
PubChem CID	445408;
UNII	ZS1409014A ;
CompTox Dashboard (EPA)	DTXSID20163348 ;
	InChI InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1 Key: DWRXFEITVBNRMK-JXOAFFINSA-N ; InChI=1/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1 Key: DWRXFEITVBNRMK-JXOAFFINBW;
	SMILES CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O;
Properties
Chemical formula	C10H14N2O6
Molar mass	258.23 g/mol
Density	1,6 g/cm3
Melting point	184 °C (363 °F; 457 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

The chemical compound 5-methyluridine (symbol m⁵U or m5U), also called ribothymidine (rT)^{[footnote 1]}, is a pyrimidine nucleoside. It is the ribonucleoside counterpart to the deoxyribonucleoside thymidine, which lacks a hydroxyl group at the 2' position. 5-Methyluridine contains a thymine base joined to a ribose pentose sugar.^[4] It is a white solid.

m5U is one of the most common modifications made to cellular RNA. It almost universally occurs in position 54 (part of the T arm) of eukaryotic and bacterial tRNA, serving to stabilize the molecule. The same "T-loop" motif occurs in many other forms of noncoding RNA such as tmRNA and rRNA. Loss of the tRNA modification does not usually produce a different, less fit, phenotype.^[5]

Footnotes

^ The term ribothymidine is especially used to describe its unusual occurrence in RNA.^[3]

References

^ "5-Methyluridine". ChemSpider. Retrieved December 6, 2018.
^ William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-400. ISBN 978-1-4987-5429-3.
^ Lehninger Principles of Biochemistry (6th ed.). W. H. Freeman and Company. 2013. p. 282. ISBN 9781429234146.
^ Shobbir Hussain (2019). "Catalytic crosslinking-based methods for enzyme-specified profiling of RNAribonucleotide modifications". Methods. 156: 60–65. doi:10.1016/j.ymeth.2018.10.003. PMID 30308313. S2CID 52961265.
^ Powell, CA; Minczuk, M (April 2020). "TRMT2B is responsible for both tRNA and rRNA m(5)U-methylation in human mitochondria". RNA Biology. 17 (4): 451–462. doi:10.1080/15476286.2020.1712544. PMC 7237155. PMID 31948311.

[0-4] The term ribothymidine is especially used to describe its unusual occurrence in RNA.^[3]

[cspider-1] "5-Methyluridine". ChemSpider. Retrieved December 6, 2018.

[crc97-2] William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-400. ISBN 978-1-4987-5429-3.

[3] Lehninger Principles of Biochemistry (6th ed.). W. H. Freeman and Company. 2013. p. 282. ISBN 9781429234146.

[5] Shobbir Hussain (2019). "Catalytic crosslinking-based methods for enzyme-specified profiling of RNAribonucleotide modifications". Methods. 156: 60–65. doi:10.1016/j.ymeth.2018.10.003. PMID 30308313. S2CID 52961265.

[6] Powell, CA; Minczuk, M (April 2020). "TRMT2B is responsible for both tRNA and rRNA m(5)U-methylation in human mitochondria". RNA Biology. 17 (4): 451–462. doi:10.1080/15476286.2020.1712544. PMC 7237155. PMID 31948311.

[1]

[2]

[footnote 1]

[4]

[5]

[3]

See also

Footnotes

References