5-Methyluridine

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5-methyluridine
)
Not to be confused with uridine, thymidine, or thymine.
5-Methyluridine
Skeletal formula of 5-methyluridine
Space-filling model of the 5-methyluridine molecule
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
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.014.522 Edit this at Wikidata
UNII
  • 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 ☒N
    Key: DWRXFEITVBNRMK-JXOAFFINSA-N ☒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
  • CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
Properties
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).
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The

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

rRNA. Loss of the tRNA modification does not usually produce a different, less fit, phenotype.[5]

See also

Footnotes

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

References

  1. ^ "5-Methyluridine". ChemSpider. Retrieved December 6, 2018.
  2. ISBN 978-1-4987-5429-3
    .
  3. ISBN 9781429234146
    .
  4. S2CID 52961265
    .
  5. PMID 31948311
    .
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