13860-38-3 Usage
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).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 13860-38-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,8,6 and 0 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13860-38:
(7*1)+(6*3)+(5*8)+(4*6)+(3*0)+(2*3)+(1*8)=103
103 % 10 = 3
So 13860-38-3 is a valid CAS Registry Number.
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)
13860-38-3Relevant articles and documents
Nucleosides. CVI. Synthesis of 1 N methyl 5 (β D ribofuranosyl)uracil (1 N methyl psi uridine) and its identity with a metabolite elaborated by Streptomyces platensis var. clarensis
Reichman,Hirota,Chu,et al.
, p. 129 - 131 (1977)
-
Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives
Chang, Yu-Cheng,Herath, Jayatilake,Wang, Tony H.-H.,Chow, Christine S.
, p. 2676 - 2686 (2008/09/21)
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.
Nucleosides. 120. Syntheses of 2'-deoxy-ψ-isocytidine and 2'-deoxy-1-methyl-ψ-uridine from ψ-uridine
Matsuda,Chu,Reichman,et al.
, p. 3603 - 3609 (2007/10/02)
-