13860-38-3

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 NO: 13860-38-3
• Molecular Formula: C₁₀H₁₄N₂O₆
• Molecular Weight: 258.229
• Mol File: 13860-38-3.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.576g/cm³
• Refractive Index: 1.618
• CAS DataBase Reference: 1-methylpseudouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methylpseudouridine(13860-38-3)
• EPA Substance Registry System: 1-methylpseudouridine(13860-38-3)

Safety Data

• Hazardous Substances Data: 13860-38-3(Hazardous Substances Data)

Usage

Uses

Used in Biotechnology and Pharmaceutical Industry:
1-Methylpseudouridine is used as a substitute for uridine in modified mRNA for various applications in the biotechnology and pharmaceutical industries. The substitution of uridine with 1-methylpseudouridine in mRNA has been shown to increase transfection efficiency by reducing immunogenicity. This is achieved by the modified mRNA's ability to evade detection by the edosomal Toll-like receptor (TLR3), which leads to lower immune stimulation and consequently, enhanced protein expression.

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.

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)

Upstream product

• 1445-07-4 pseudouridine 
• 74-88-4 methyl iodide 
• 61289-19-8 N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine 
• 24800-34-8 5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrimidine-2,4-(1H,3H)-dione 
• 1024616-73-6 1-methyl-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-(isopropylidene)pseudouridine 
• 63064-72-2 (4R)-2,2-dimethyl-(3at,11at)-3a,4,5,7⁽⁹⁾,11,11a-hexahydro-4r,11c-epioxido-[1,3]dioxolo[4',5':5,6]oxocino[2,3-d]pyrimidin-8-one 

Downstream Products

• 127517-32-2 1-methyl-2'-O-tosylpseudouridine 
• 127517-33-3 1-methyl-3'-O-tosylpseudouridine 
• 65358-15-8 Pseudothymidine 
• 136804-01-8 N1-methyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-ψ-uridine 
• 162604-96-8 N1-methyl-2'-O-allyl-5'-O-(4,4'-dimethoxytrityl)-ψ-uridine 
• 78064-64-9 1-methyl-2'-deoxy-5'-O-tritylpseudouridine 
• 78064-63-8 2',3'-Didehydro-2',3'-dideoxy-1-methyl-5'-O-tritylpseudouridine 
• 78109-46-3 3'-Deoxy-1-methyl-5'-O-tritylpseudouridine 
• 78064-66-1 1,3-Dimethyl-2'-deoxy-5'-O-tritylpseudouridine 
• 78064-62-7 1-Methyl-2',3'-O-(thionocarbonyl)-5'-O-tritylpseudouridine 
• 78064-68-3 5'-O-Trityl-2'-deoxy-α-ψ-isocytidine 
• 78064-67-2 5'-O-Trityl-2'-deoxy-ψ-isocytidine 
• 65358-18-1 2'-Deoxy-ψ-isocytidine 
• 875302-39-9 5'-O-(4,4'-dimethoxitrityl)-1-N-methylpseudouridine 

Relevant articles and documents

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

A series of 3-substituted uridine and pseudouridine derivatives, based on the naturally occurring 3-(3-amino-3-carboxypropyl) modification, were synthesized. Their aqueous solution conformations were determined by using circular dichroism and NMR spectroscopy. Functional group composition and chain length were shown to have only a subtle influence on the distribution of syn/anti conformations of the modified nucleosides. The dominating factor appears to be the glycosidic linkage (C- vs. N-glycoside) in determining the nucleoside conformation.

A practical synthesis of N1-methyl-2'-deoxy-ψ-uridine (ψ-thymidine) and its incorporation into G-rich triple helix forming oligonucleotides

A convenient synthesis of N1-methyl-2'-deoxy-ψ-uridine (ψ-thymidine, ψT, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich triplex f