プソイドウリジン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/02/02 21:58:16」(JST)
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Pseudouridine
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Names |
IUPAC name
5-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)-oxolan-2-yl]-1H-pyrimidine-2,4-dione
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Preferred IUPAC name
5-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione
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Other names
psi-Uridine, 5-Ribosyluracil, beta-D-Pseudouridine, 5-(beta-D-Ribofuranosyl)uracil
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Identifiers |
CAS Number
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1445-07-4 N |
ChEBI |
CHEBI:17802 Y |
ChemSpider |
14319 Y |
Jmol interactive 3D |
Image |
PubChem |
15047 |
InChI
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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 Y
Key: PTJWIQPHWPFNBW-GBNDHIKLSA-N Y
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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
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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
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SMILES
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O=C1N\C=C(/C(=O)N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
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Properties |
Chemical formula
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C9H12N2O6 |
Molar mass |
244.20 g/mol |
Appearance |
White granular powder |
Solubility in water
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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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N verify (what is YN ?) |
Infobox references |
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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]
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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]
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A tRNAAla from S. cerevisiae.
Pseudouridine =
Ψ
See also
- Pseudouridine kinase
- TRNA-pseudouridine synthase
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
UpToDate Contents
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English Journal
- Reparameterizations of the χ Torsion and Lennard-Jones σ Parameters Improve the Conformational Characteristics of Modified Uridines.
- Deb I1,2, Pal R1, Sarzynska J2, Lahiri A1.
- Journal of computational chemistry.J Comput Chem.2016 Jun 30;37(17):1576-88. doi: 10.1002/jcc.24374. Epub 2016 Mar 30.
- The currently available force field parameters for modified RNA residues in AMBER show significant deviations in conformational properties from experimental observations. The examination of the transferability of the recently revised torsion parameters revealed that there was an overall improvement
- PMID 27030560
- Structural Basis for Translation Termination on a Pseudouridylated Stop Codon.
- Svidritskiy E1, Madireddy R1, Korostelev AA2.
- Journal of molecular biology.J Mol Biol.2016 May 22;428(10 Pt B):2228-2236. doi: 10.1016/j.jmb.2016.04.018. Epub 2016 Apr 20.
- Pseudouridylation of messenger RNA emerges as an abundant modification involved in gene expression regulation. Pseudouridylation of stop codons in eukaryotic and bacterial cells results in stop-codon read through. The structural mechanism of this phenomenon is not known. Here we present a 3.1-Å cry
- PMID 27107638
- Pseudouridine synthase 1 deficient mice, a model for Mitochondrial Myopathy with Sideroblastic Anemia, exhibit muscle morphology and physiology alterations.
- Mangum JE1, Hardee JP1, Fix DK1, Puppa MJ1, Elkes J2, Altomare D3, Bykhovskaya Y4, Campagna DR5, Schmidt PJ5, Sendamarai AK5, Lidov HG5, Barlow SC6, Fischel-Ghodsian N4, Fleming MD5, Carson JA1, Patton JR2.
- Scientific reports.Sci Rep.2016 May 20;6:26202. doi: 10.1038/srep26202.
- Mitochondrial myopathy with lactic acidosis and sideroblastic anemia (MLASA) is an oxidative phosphorylation disorder, with primary clinical manifestations of myopathic exercise intolerance and a macrocytic sideroblastic anemia. One cause of MLASA is recessive mutations in PUS1, which encodes pseudo
- PMID 27197761
Japanese Journal
- Functional Analysis of the C-Terminal Region of γ-Glutamyl Kinase of Saccharomyces cerevisiae
- Bioscience, biotechnology, and biochemistry 76(3), 454-461, 2012-03-23
- NAID 10030750315
- Pseudouridine detection improvement by derivatization with methyl vinyl sulfone and capillary HPLC-mass spectrometry
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 825(2), 233-238, 2005-10-25
- NAID 10016978007
- 健常新生児および尿素サイクル異常症における尿中ピリミジン分析
Related Links
- 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, ...
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