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13860-38-3

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    Cas No: 13860-38-3

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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)

13860-38-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-methylpseudouridine

1.2 Other means of identification

Product number -
Other names 1-Methylpseudouridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13860-38-3 SDS

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)

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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)

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