Pseudouridine

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Pseudouridine
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
CAS number 1445-07-4 YesY
PubChem 15047
ChemSpider 14319 YesY
ChEBI CHEBI:17802 YesY
Jmol-3D images {{#if:O=C1N\C=C(/C(=O)N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O|Image 1
Properties
Molecular formula C9H12N2O6
Molar mass 244.20 g/mol
Appearance White granular powder
Solubility in water Highly soluble in water.
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 except mRNA.[2][3] Ψ is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation.[4]

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.[5]

A tRNAAla from S. cerevisiae.
Pseudouridine = Ψ

See also

References

  1. ↑ Hamma T, Ferré-D'Amaré AR (2006). "Pseudouridine synthases". Chem. Biol. 13 (11): 1125–1135. doi:10.1016/j.chembiol.2006.09.009. PMID 17113994. 
  2. ↑ Charette M, Gray MW (2000). "Pseudouridine in RNA: what, where, how, and why". IUBMB Life 49 (5): 341–351. doi:10.1080/152165400410182. PMID 10902565. 
  3. ↑ Liang XH, Xu YX, MIchaeli S (2002). "The spliced leader-associated RNA is a trypanosome-specific sn(o) RNA that has the potential to guide pseudouridine formation on the SL RNA". RNA 8 (2): 237–246. doi:10.1017/S1355838202018290. PMC 1370245. PMID 11911368. 
  4. ↑ Ferré-D'Amaré AR (2003). "RNA-modifying enzymes". Curr. Opin. Struct. Biol. 13 (1): 49–55. doi:10.1016/S0959-440X(02)00002-7. PMID 12581659. 
  5. ↑ Monobe, Manami; Arimoto-Kobayashi, Sakae; Ando, Koichi (2003). "β-Pseudouridine, a beer component, reduces radiation-induced chromosome aberrations in human lymphocytes". Mutation research. Genetic toxicology and environmental mutagenesis 538 (1–2): 93–99. doi:10.1016/S1383-5718(03)00094-9. PMID 12834758. 
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