5-Methyluridine
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Names | |
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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 | |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.014.522 ![]() |
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InChI
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Properties | |
Chemical formula | C10H14N2O6 |
Molar mass | 258.23 g/mol |
Density | 1,6 g/cm3[1] |
Melting point | 184[2] °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). ![]() ![]() ![]() 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]
See also
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.
- v
- t
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- Purine
- Pyrimidine
- Unnatural base pair (UBP)
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Deoxyribonucleoside |
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(Nucleoside monophosphate)
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Deoxyribonucleotide | |
Cyclic nucleotide |