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
References
- Monobe M., et al., β-Pseudouridine, a beer component, reduces radiation-induced chromosome aberrations in human lymphocytes, Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2003, 538(1-2): 93-99.
- Barát V., et al., An improved stereodivergent and practical synthesis of α-and β-pseudouridines, Reaction Chemistry & Engineering, 2023, 8(4): 798-803.
- Deslauriers R., et al., A comparison of the conformations of uridine, β-pseudouridine, and dihydrouridine in dimethyl sulfoxide and water. A 1H nuclear magnetic resonance study, Canadian Journal of Chemistry, 1973, 51(6): 833-838.
- Hanessian S., et al., A highly stereocontrolled and efficient synthesis of α-and β-pseudouridines, Tetrahedron Letters, 2003, 44(45): 8321-8323.
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Chemical Structure
