β-pseudoUridine - CAS 1445-07-4
An isomer of the nucleoside uridine found in all species and in many classes of RNA except mRNA. It is formed by enzymes called synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation. Studies suggest that Beta-Pseudouridine reduces radiation-induced chromosome aberrations in human lymphocytes.
Catalog Number
B2000-084156
CAS
1445-07-4
Molecular Weight
244.20
Molecular Formula
C9H12N2O6
Symbol
Ψ
Synonyms
Pseudouridine; ψ-Uridine; 5-(β-D-Ribofuranosyl)uracil; b-pseudoUridine; 5-β-D-Ribofuranosyl-2,4(1H,3H)-Pyrimidinedione; 5-Ribosyluracil; NSC 162405; Pseudouridine C; β-D-Pseudouridine; 5-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
IUPAC Name
5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione
Canonical SMILES
C1=C(C(=O)NC(=O)N1)C2C(C(C(O2)CO)O)O
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
InChIKey
PTJWIQPHWPFNBW-GBNDHIKLSA-N
Boiling Point
598.4±60.0 °C at 760 mmHg
Melting Point
212-214°C
Purity
98%
Density
1.641±0.06 g/cm3 (Predicted)
Solubility
Soluble in Methanol (Very Slightly, Heated), Water (Slightly, Sonicated, Heated)
Appearance
White to Off-white Solid
Storage
Store at 2-8°C
Symbol
Ψ
1.Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism.
Tavazzi B1, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1.
OBJECTIVES: To set up a novel simple, sensitive, and reliable ion-pairing HPLC method for the synchronous separation of several purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis and screening of inborn errors of metabolism (IEM).
2.Beta-pseudouridine, a beer component, reduces radiation-induced chromosome aberrations in human lymphocytes.
Monobe M1, Arimoto-Kobayashi S, Ando K. Mutat Res. 2003 Jul 8;538(1-2):93-9.
We previously found that drinking beer reduces chromosome aberrations in blood lymphocytes that were collect and irradiated in vitro. In this study, human whole-blood was in vitro exposed to 200kVp X-rays or 50keV/microm carbon ions in the presence or absence of beer, ethanol and beta-pseudouridine (one of the beer components). All three agents reduced the chromosome aberrations (dicentric) caused by either X-rays or carbon ions of 4Gy. The maximum protection for X-rays by ethanol, beer and beta-pseudouridine was 64, 26 and 34%, respectively, while the maximum protection for carbon-ion by ethanol, beer and beta-pseudouridine was 22, 26 and 32%, respectively. It is concluded that beta-pseudouridine, a nucleoside present in tRNA, is a potent protector against damage caused by radiation with direct and indirect actions.
3.Serum metabolic profile in multiple sclerosis patients.
Tavazzi B1, Batocchi AP, Amorini AM, Nociti V, D'Urso S, Longo S, Gullotta S, Picardi M, Lazzarino G. Mult Scler Int. 2011;2011:167156. doi: 10.1155/2011/167156. Epub 2011 Jun 28.
Multiple sclerosis (MS) is a progressive demyelinating process considered as an autoimmune disease, although the causes of this pathology have not been yet fully established. Similarly to other neurodegenerations, MS is characterized by a series of biochemical changes affecting to different extent neuronal functions; great attention has been given to oxidative/nitrosative stress and to alterations in mitochondrial functions. According to previous data, MS patients show significant changes in the circulating concentrations of different metabolites, although it is still unclear whether uric acid undergoes to decrease, increase, or no change under this pathological condition. In this study, we report the serum metabolic profile in terms of purines, pyrimidines, creatinine, malondialdehyde, ascorbic acid, nitrite, and nitrate in a group of 170 MS patients. The results show increase in circulating uric acid and other oxypurines (hypoxanthine and xanthine), as well as in uridine and β-pseudouridine.
4.A nuclear magnetic resonance study of the molecular conformation of beta-pseudouridine in aqueous solution.
Hruska FE, Grey AA, Smith IC. J Am Chem Soc. 1970 Jul 1;92(13):4088-94.
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