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Pseudouridine

Pseudouridine Structural

What is Pseudouridine?

Description

β-Pseudouridine 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. 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.

The Uses of Pseudouridine

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.

What are the applications of Application

β-Pseudouridine is a compound also known as 5-β-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione

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].

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.

Properties of Pseudouridine

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
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

Safety information for Pseudouridine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Pseudouridine

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|

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