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| | 1-methylpseudouridine Basic information |
| Product Name: | 1-methylpseudouridine | | Synonyms: | 1-methylpseudouridine;(-)-1-Methyl-5-(β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione;1-Methyl-5-(β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione;1-Methyl-5-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione;Antibiotic U-50228;U-50228;N1-Methylpseudouridine;1-N-ME-PSEUDOURIDINE | | CAS: | 13860-38-3 | | MF: | C10H14N2O6 | | MW: | 258.229 | | EINECS: | | | Product Categories: | Pharmaceutical;Nucleotides;Nucleosides | | Mol File: | 13860-38-3.mol |  |
| | 1-methylpseudouridine Chemical Properties |
| density | 1.576±0.06 g/cm3(Predicted) | | storage temp. | Store at -20°C | | solubility | >20 mg/mL in EtOH; >20.65 mg/mL in DMSO | | pka | 9.43±0.10(Predicted) | | form | A solid | | Water Solubility | insoluble in Water; | | InChI | InChI=1/C10H14N2O6/c1-12-2-4(9(16)11-10(12)17)8-7(15)6(14)5(3-13)18-8/h2,5-8,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,8+/s3 | | InChIKey | UVBYMVOUBXYSFV-CAYFCZNJNA-N | | SMILES | [C@@H]1(O)[C@@H](CO)O[C@@H](C2C(=O)NC(=O)N(C)C=2)[C@@H]1O |&1:0,2,6,16,r| |
| | 1-methylpseudouridine Usage And Synthesis |
| Description | N1-Methylpseudouridine is a modified nucleoside used for enhancing mRNA translation. Incorporation of N1-Methylpseudouridine into mRNA turns off the immune/eIF2α phosphorylation-dependent inhibition of translation, and increases ribosome pausing and density on the mRNA, thus dramatically facilitating the translation process. N1-Methylpseudouridine outperforms several other modified nucleosides (e.g. 5-Methylcytidine) and corresponding combinations in terms of translation capacity. | | Definition | ChEBI: 1-methylpseudouridine is a methylpseudouridine in which the methyl group is located at position N-1 on the uracil ring. | | Application | 1-Methylpseudouridine is a substitute for uridine in modified mRNA. This substitution has shown to increase transfection by reducing immuogenicity. The 1-methylpseudouridine substituted mRNA increases protein expression due to low immune stimulation as it evades detection by the edosomal Toll-like receptor (TLR3). | | Advantages | N1-Methylpseudouridine is the methylated derivative of pseudouridine. It is used in in vitro transcription and for the production of RNA vaccines.In vertebrates, it stimulates significantly less activation of the innate immune response compared to uridine,while the translation is stronger.In protein biosynthesis, it is read like uridine and enables comparatively high protein yields.The nucleoside itself can be made by chemical methylation of pseudouridine. | | References | 1. Svitkin YV, Cheng YM, Chakraborty T, et al. N1-methyl-pseudouridine in mRNA enhances translation through eIF2α-dependent and independent mechanisms by increasing ribosome density. Nucleic Acids Research, 2017, 45(10): 6023-6036.
2. Andries O, Mc Cafferty S, De Smedt SC, et al N(1)-methylpseudouridine-incorporated mRNA outperforms pseudouridine-incorporated mRNA by providing enhanced protein expression and reduced immunogenicity in mammalian cell lines and mice. Journal of Controlled Release, 2015, 217: 337-344. |
| | 1-methylpseudouridine Preparation Products And Raw materials |
| Raw materials | 2,4(1H,3H)-Pyrimidinedione, 1-methyl-5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)--->2,4(1H,3H)-Pyrimidinedione, 5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)--->2,4(1H,3H)-Pyrimidinedione, 5-[5-O-[(1,1-dimethylethyl)diphenylsilyl]-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl]-1-methyl- |
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