| Identification | Back Directory | [Name]
BETA-PSEUDOURIDINE | [CAS]
1445-07-4 | [Synonyms]
y-Uridine
NSC 162405
PSEUDOURIDINE
Pseudourindine
β-Pseudouridine
B-Pseudouridine
Pseudouridine C
5-Ribosyluracil
β-D-Pseudouridine
BETA-PSEUDOURIDINE
5-β-D-ribofuranosyluracil
Uridine Impurity 20（β-Pseudouridine）
5-β-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione
5-b-D-ribofuranosyl-2,4(1H,3H)-Pyrimidinedione
2,4(1H,3H)-Pyrimidinedione, 5-β-D-ribofuranosyl-
2,4(1H,3H)-PyriMidinedione, 5-b-D-ribofuranosyl-
5-β-D-Ribofuranosyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
5-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione | [Molecular Formula]
C9H12N2O6 | [MDL Number]
MFCD00038458 | [MOL File]
1445-07-4.mol | [Molecular Weight]
244.2 |
| Chemical Properties | Back Directory | [Melting point ]
222 °C | [density ]
1.641±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Methanol (Very Slightly, Heated), Water (Slightly, Sonicated, Heated) | [form ]
Solid | [pka]
8.52±0.10(Predicted) | [color ]
White to Off-White | [PH]
～9.0 | [biological source]
synthetic (chemical) | [Water Solubility ]
water: soluble | [λmax]
264nm(MeOH)(lit.) | [InChI]
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+/s3 | [InChIKey]
PTJWIQPHWPFNBW-IZFRNLNUNA-N | [SMILES]
O[C@@H]1[C@@H]([C@@H](CO)O[C@H]1C1=CNC(=O)NC1=O)O |&1:1,2,3,7,r| |
| Hazard Information | Back Directory | [Description]
β-Pseudouridine(1445-07-4) is the C-5 glycoside isomer of the nucleoside uridine . It is formed when uridine in RNA undergoes site-specific isomerization by a pseudouridine synthase enzyme. β-pseudouridine is found in tRNAs from bacteria, archaea, and eukaryotes. In vitro, it reduces the number of X-ray-induced chromosomal aberrations in human lymphocytes isolated from whole blood in a dose-dependent manner. | [Uses]
An isomer of the nucleoside uridine found in all species and in many classes of RNA except mRNA. It is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation. Studies suggest that β-Pseudouridine reduces radiation-induced chromosome aberrations in human lymphocytes. | [Definition]
ChEBI: Pseudouridine is a C-glycosyl pyrimidine that consists of uracil having a beta-D-ribofuranosyl residue attached at position 5. The C-glycosyl isomer of the nucleoside uridine. It has a role as a fundamental metabolite. | [Origin]
Pseudouridine (Ψ) was the first modified ribonucleotide discovered 7 decades ago, and it has been found in tRNA, rRNA, snRNA, mRNA, and other types of RNA[2]. | [Biochem/physiol Actions]
Pseudouridine is essential for rRNA folding and for regulating translational accuracy and it is required for stabilizing the tRNA structure. Pseudouridine in rRNA and tRNA has been shown to fine-tune and stabilize the regional structure and help maintain their functions in mRNA decoding, ribosome assembly, processing and translation. Pseudouridine in snRNA has been shown to enhance spliceosomal RNA-pre-mRNA interaction to facilitate splicing regulation[1].
| [Enzyme inhibitor]
This pseudonucleoside (FW = 244.20 g/mol), also known as 5-D-b-
ribofuranosyluracil and 5-D-b-ribosyluracil and symbolized by y, is a
nonglycosidic constituent of tRNA and snRNA. The lmax value at pH 7 is
263 nm (e = 8100 M–1cm–1); the value at pH 12 is 286 nm (e = 7700 M–1cm–
and UDP-N-acetylglucosamine diphosphorylase, or N-acetylglucosamine-1-
phosphate uridylyltransferase. | [target]
Human Endogenous Metabolite | [Structure and conformation]
Pseudouridine, being one of them, is the C5-glycoside isomer of uridine that contains a C-C bond between C1 of the ribose sugar and C5 of uracil, rather than usual C1-N1 bond found in uridine. The C-C bond gives it more rotational freedom and conformational flexibility.In addition, pseudouridine has an extra hydrogen bond donor at the N1 position.
| [References]
[1] Mingjia Chen, Claus-Peter Witte. “A Kinase and a Glycosylase Catabolize Pseudouridine in the Peroxisome to Prevent Toxic Pseudouridine Monophosphate Accumulation.” Plant Cell 32 3 (2020): 722–739.
[2] Pedro Morais, Yi-Tao Yu, Hironori Adachi. “The Critical Contribution of Pseudouridine to mRNA COVID-19 Vaccines.” Frontiers in Cell and Developmental Biology (2021): 789427. |
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