• 21 MAY 20
    Pseudouridine

    Pseudouridine

    Application Pseudouridine (abbreviated by the Greek letter psi- Ψ or the letter Q) is an isomer of the nucleoside uridine in which the uracil is attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond. (In this configuration, uracil is sometimes referred to as ‘pseudouracil’.) It is the most abundant RNA modification in cellular RNA. After transcription and following synthesis, RNA can be modified with over 100 chemically distinct modifications. These can potentially regulate RNA expression post-transcriptionally, in addition to the four standard nucleotides and play a variety of roles in the cell including translation, localization and stabilization of RNA. 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, it has an extra hydrogen bond donor at the N1 position. Also known as 5-ribosyluracil, it is a ubiquitous yet enigmatic constituent of structural RNAs (transfer, ribosomal, small nuclear (snRNA) and small nucleolar). Recently it has also been discovered in coding RNA. Being the most abundant, it is found in all 3 phylogenetic domains of life and was the first to be discovered. This nucleotide is considered to be the “fifth nucleotide”. It accounts for 4% of the nucleotides in the yeast tRNA. This base modification is able to stabilize RNA and improve base-stacking by forming additional hydrogen bonds with water through its extra imino group. There are 11 ones in the Escherichia coli rRNA, 30 in yeast cytoplasmic rRNA and a single modification in mitochondrial 21S rRNA and about 100 ones in human rRNA indicating that the extent of pseudouridylation increases with the complexity of an organism. 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.

    Synonyms (1S)-1,4-Anhydro-1-(2,4-dihydroxy-5-pyrimidinyl)-D-ribitol [German] [ACD/IUPAC Name]; (1S)-1,4-Anhydro-1-(2,4-dihydroxy-5-pyrimidinyl)-D-ribitol [ACD/IUPAC Name]; (1S)-1,4-Anhydro-1-(2,4-dihydroxy-5-pyrimidinyl)-D-ribitol [French] [ACD/IUPAC Name]; (1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-D-ribitol [ACD/IUPAC Name]; (1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-D-ribitol [German] [ACD/IUPAC Name]; (1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tétrahydro-5-pyrimidinyl)-D-ribitol [French] [ACD/IUPAC Name]; 2,4(1H,3H)-Pyrimidinedione, 5-β-D-ribofuranosyl-; 2,4(1H,3H)-Pyrimidinedione, 5-β-D-ribofuranosyl-; 5-(b-D-Ribofuranosyl)uracil; 5-b-D-ribofuranosyl-Uracil; D-Ribitol, 1,4-anhydro-1-C-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl)-, (1S)- [ACD/Index Name]; D-Ribitol, 1,4-anhydro-1-C-(2,4-dihydroxy-5-pyrimidinyl)-, (1S)- [ACD/Index Name]; Uracil, 5-β-D-ribofuranosyl-; 5-(b-δ-Ribofuranosyl)uracil; 5-β-δ-ribofuranosyl-Uracil; b-D-Pseudouridine; b-Pseudouridine; y-Uridine; β-δ-Pseudouridine; (1S)-1,4-anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-D-ribitol; 2,4(1H,3H)-Pyrimidinedione, 5-β-D-ribofuranosyl; 5-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; 5-(b-D-Ri bofuranosyl)uracil; 5-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione; 5-(β-D-Ribofuranosyl)uracil; 5-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione; 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione; 5-Ribosyluracil; Pseudouridine C; Uracil, 5-β-D-ribofuranosyl- (6CI,7CI,8CI); β-D-Pseudouridine; β-Pseudouridine; ψ-uridine; ψ-Uridine

    CAS Number 1445-07-4 | Molecular Formula C9H12N2O6 | Molecular Weight 244.2

    SMILES c1c(c(nc(n1)O)O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

    StdInChI 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

    StdInChIKey PTJWIQPHWPFNBW-GBNDHIKLSA-N

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