81691-06-7 Usage
Description
3-Methylpseudouridine is a modified nucleoside that plays a crucial role in enhancing the stability and functionality of RNA molecules, particularly in the context of modified mRNAs used for protein expression.
Uses
Used in Biotechnology and Pharmaceutical Industry:
3-Methylpseudouridine is used as a stabilizing agent for increasing the viability or longevity of organs or organ explants by enhancing the stability and translational efficiency of modified mRNAs encoding proteins essential for organ survival.
Used in mRNA Therapeutics and Vaccines:
3-Methylpseudouridine is utilized as a key component in the development of mRNA-based therapeutics and vaccines, where it contributes to the improved performance and safety of these treatments by enhancing mRNA stability and reducing the risk of immune-related adverse effects.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 81691-06-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,6,9 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 81691-06:
(7*8)+(6*1)+(5*6)+(4*9)+(3*1)+(2*0)+(1*6)=137
137 % 10 = 7
So 81691-06-7 is a valid CAS Registry Number.
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)
81691-06-7Relevant articles and documents
Synthesis of helix 69 of Escherichia coli 23S rRNA containing its natural modified nucleosides, m(3)Psi and Psi.
Chui, Helen M-P,Desaulniers, Jean-Paul,Scaringe, Stephen A,Chow, Christine S
, p. 8847 - 8854 (2007/10/03)
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.
