81691-06-7

Basic information

• Product Name: 3-methylpseudouridine
• Synonyms: 3-methylpseudouridine;NSC 363818;3-Methyl-5-beta-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione;3-Methylpsedouridine
• CAS NO: 81691-06-7
• Molecular Formula: C10H14N2O6
• Molecular Weight: 258.22796
• Mol File: 81691-06-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.576g/cm³
• Refractive Index: 1.618
• CAS DataBase Reference: 3-methylpseudouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylpseudouridine(81691-06-7)
• EPA Substance Registry System: 3-methylpseudouridine(81691-06-7)

Safety Data

• Hazardous Substances Data: 81691-06-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 81691-06-7 differently. You can refer to the following data:
1. 3-Methylpseudouridine is used for increasing viability or longevity of organ or organ explant using modified mRNAs for proteins essential for organ survival.
2. 3-Methylpseudouridine (CAS# 81691-06-7) is used for increasing viability or longevity of organ or organ explant using modified mRNAs for proteins essential for organ survival.

Synthesis

ψ-Uridine was trimethylsilylated and the crude product was treated with acetyl chloride, to give the 1-acetyl derivative (3). Crude 3 was methylated with dimethoxymethyldimethylamine and then saponified, to give crystalline 3-methyl-ψ-uridine in 82% overall yield.

InChI:InChI=1/C10H14N2O6/c1-12-9(16)4(2-11-10(12)17)8-7(15)6(14)5(3-13)18-8/h2,5-8,13-15H,3H2,1H3,(H,11,17)

Upstream product

• 81691-07-8 3-methyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)pseudouridine 
• 81691-04-5 1-acetyl-2',3',5'-tri-O-trimethylsilyl-ψ-uridine 
• 482643-84-5 1-pivaloyloxymethyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)pseudouridine 
• 482643-86-7 3-methyl-1-pivaloyloxymethyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)pseudouridine 
• 482643-88-9 3-methyl-1-pivaloyloxymethyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)pseudouridine 
• 164300-60-1 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)pseudouridine 
• 1445-07-4 pseudouridine 
• 80545-49-9 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)pseudouridine 
• 81691-05-6 1-Acetyl-5-((2S,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 81691-10-3 2'-deoxy-3-methyl-ψ-uridine 

Relevant articles and documents

Synthesis of helix 69 of Escherichia coli 23S rRNA containing its natural modified nucleosides, m(3)Psi and Psi.

The synthesis of 3-methylpseudouridine (m(3)Psi) phosphoramidite, 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine-3'-(methyl-N,N-diisopropyl)phosphoramidite, is reported. Selective pivaloyloxymethyl protection of the Psi N1 followed by methylation at N3 was used to generate the naturally occurring pseudouridine analogue. The m(3)Psi phosphoramidite was used in combination with pseudouridine (Psi) and standard base phosphoramidites to synthesize a 19-nucleotide RNA representing helix 69 of Escherichia coli 23S ribosomal RNA (rRNA) (residues 1906-1924), containing a single m(3)Psi at position 1915 and two Psi's at positions 1911 and 1917. Our synthesis of the fully modified helix 69 RNA demonstrates the ability to make milligram quantities of RNA that can be used for further high-resolution structure studies. Site-selective introduction of the methyl group at the N3 position of pseudouridine at position 1915 causes a slight increase in the thermodynamic stability of the RNA hairpin relative to pseudouridine; RNAs containing either uridine or 3-methyluridine at position 1915 have similar stability. One-dimensional imino proton NMR and circular dichroism spectra of the modified RNAs reveal that the methyl group does not cause any substantial changes in the RNA hairpin structure.