α-Pseudouridine Chemical Properties

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-DVJSAIJENA-N

SMILES

C1(=O)NC=C([C@@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C(=O)N1 |&1:5,6,8,10,r|

α-Pseudouridine Usage And Synthesis

Description

Alpha-pseudouridine is an unusual nucleoside with a "glycosidic" carbon-carbon bond.

Uses

Alpha-Pseudouridine is an isomer of Pseudouridine. It is a by-product of the chemical synthesis of beta-pseudouridine, is eliminated in EnginZyme’s enzymatic synthesis process. Pseudouridine is a fundamental component of RNA, found in all classes and species except the messenger (mRNA) variety. It most abundant RNA modification, found in all three phylogenic domains of life. When used in place of uridine in artificial mRNA, pseudouridine has proven to be critical to the success of mRNA vaccines (such as those for Covid-19) and future mRNA-based treatments.

References

[1] BARáT V, CHEN A, LIM Y H. An improved stereodivergent and practical synthesis of α- and β-pseudouridines?[J]. Reaction Chemistry & Engineering, 2022, 4: 798-803. DOI:10.1039/D2RE00381C.
[2] HAIQI XU. Absolute quantitative and base-resolution sequencing reveals comprehensive landscape of pseudouridine across the human transcriptome[J]. Nature Methods, 2024, 21 11: 2024-2033. DOI:10.1038/s41592-024-02439-8.
[3] MARTIN HENGESBACH. Formation of a stalled early intermediate of pseudouridine synthesis monitored by real-time FRET.[J]. RNA, 2010, 16 3: 610-620. DOI:10.1261/rna.1832510.