Pseudouridine

Pseudouridine

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
CAS Number	1445-07-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17802
ChemSpider	14319
PubChem	15047
InChI 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 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
SMILES O=C1N\C=C(/C(=O)N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
Properties
Chemical formula	C9H12N2O6
Molar mass	244.20 g/mol
Appearance	White granular powder
Solubility in water	Highly soluble in water.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pseudouridine (abbreviated by the Greek letter psi- Ψ) is an isomer of the nucleoside uridine in which the uracil is attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond. 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]

A tRNA^Ala from S. cerevisiae.
Pseudouridine = Ψ

See also

• Pseudouridine kinase
• TRNA-pseudouridine synthase

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. Carlile, Thomas (2014-09-05). "Pseudouridine profiling reveals regulated mRNA pseudouridylation in yeast and human cells". Nature. 515: 143–6. doi:10.1038/nature13802. PMID 25192136.
5. Schwartz, Schraga (2014-09-11). "Transcriptome-wide Mapping Reveals Widespread Dynamic-Regulated Pseudouridylation of ncRNA and mRNA". Cell. 159: 148–62. doi:10.1016/j.cell.2014.08.028. PMID 25219674.
6. 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.
7. 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.