Pseudouridine

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Pseudouridine
150px
Names
IUPAC name
5-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)-oxolan-2-yl]-1H-pyrimidine-2,4-dione
Preferred IUPAC name
5-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione
Other names
psi-Uridine, 5-Ribosyluracil, beta-D-Pseudouridine, 5-(beta-D-Ribofuranosyl)uracil
Identifiers
1445-07-4 N
ChEBI CHEBI:17802 YesY
ChemSpider 14319 YesY
Jmol 3D model Interactive image
PubChem 15047
  • InChI=1S/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1 YesY
    Key: PTJWIQPHWPFNBW-GBNDHIKLSA-N YesY
  • InChI=1/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1
    Key: PTJWIQPHWPFNBW-GBNDHIKLBY
  • InChI=1S/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1
    Key: PTJWIQPHWPFNBW-GBNDHIKLSA-N
  • O=C1N\C=C(/C(=O)N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
Properties
C9H12N2O6
Molar mass 244.20 g/mol
Appearance White granular powder
Highly soluble in water.
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Pseudouridine (abbreviated by the Greek letter psi- Ψ) is the C-glycoside isomer of the nucleoside uridine, and it is the most prevalent of the over one hundred different modified nucleosides found in RNA.[1] Ψ is found in all species and in many classes of RNA.[2][3] [4][5] Ψ is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation.[6]

Pseudouridine is biosynthesized from uridine via the action of Ψ synthases.

It is commonly found in tRNA, associated with thymidine and cytosine in the TΨC arm and is one of the invariant regions of tRNA.The function of it is not very clear, but it is expected to play a role in association with aminoacyl transferases during their interaction with tRNA, and hence in the initiation of translation. Recent studies suggest it may offer protection from radiation.[7]

File:TRNA-Ala yeast.svg
A tRNAAla from S. cerevisiae.
Pseudouridine = Ψ

See also

References

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