1-Methylpseudouridine

Base Information

• Chemical Name: 1-Methylpseudouridine
• CAS No.: 13860-38-3
• Molecular Formula: C10H14 N2 O6
• Molecular Weight: 258.231
• UNII: 09RAD4M6WF
• DSSTox Substance ID: DTXSID50160724
• Nikkaji Number: J13.862B
• Wikipedia: N1-Methylpseudouridine
• Wikidata: Q27109108
• Metabolomics Workbench ID: 53669
• Mol file: 13860-38-3.mol

Synonyms:1-methylpseudouridine;N1-methyl-pseudouridine

Chemical Property of 1-Methylpseudouridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 124.78000
• Density: 1.576g/cm³
• LogP: -2.77240
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 258.08518617
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

99.3% ^*data from raw suppliers

1-Methylpseudouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CN1C=C(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• 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.

Technology Process of 1-Methylpseudouridine

There total 9 articles about 1-Methylpseudouridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-methyl-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-(isopropylidene)pseudouridine (1024616-73-6) → N1-methylpseudouridine (13860-38-3)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2007.11.039

Reference yield: 90.0%

N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine (61289-19-8) → N1-methylpseudouridine (13860-38-3)

Guidance literature:

With ammonia; In methanol; for 24h; Ambient temperature;

DOI:10.1080/15257779508010690

Reference yield:

pseudouridine (1445-07-4) + methyl iodide (74-88-4) → N1-methylpseudouridine (13860-38-3)

Guidance literature:

Multistep reaction; (i) HN(SiMe3)2, 2SO4, (ii) /BRN= 969135/, MeCN, (iii) NH3, MeOH;

DOI:10.7164/antibiotics.30.129

upstream raw materials:

pseudouridine

methyl iodide

N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine

5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrimidine-2,4-(1H,3H)-dione

Downstream raw materials:

1-methyl-2'-O-tosylpseudouridine

1-methyl-3'-O-tosylpseudouridine

5'-O-(4,4'-dimethoxitrityl)-2'-O-(tert-butyldimethylsilyl)-1-methylpseudouridine 3'-O-caynoethyl-N,N-diisopropylphosphoramidate

5'-O-(4,4'-dimethoxitrityl)-3'-O-(tert-butyldimethylsilyl)-1-methylpseudouridine 3'-O-caynoethyl-N,N-diisopropylphosphoramidate

Refernces

• 1、 -. "SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS". . . Retrieved 2019/01/15.
• 2、 Bhattacharya,Devivar,Revankar. "A practical synthesis of N1-methyl-2'-deoxy-ψ-uridine (ψ-thymidine) and its incorporation into G-rich triple helix forming oligonucleotides". . p. 1269 - 1287. Retrieved 2007/10/02.