1-methylpseudouridine

ChemicalBook > CAS DataBase List > 1-methylpseudouridine

1-methylpseudouridine

Product Name: 1-methylpseudouridine
CAS No.: 13860-38-3
Chemical Name: 1-methylpseudouridine
Synonyms: U-50228;Antibiotic U-50228;N1-Me-Pseudouridine;1-N-ME-PSEUDOURIDINE;N1-methylpseudourine;Nl-methylpseudourine;1-methylpseudouridine;1-Methyipseudouridine;N1-methylpeudouridine;N1-Methylpseudouridine
CBNumber: CB01347548
Molecular Formula: C10H14N2O6
Formula Weight: 258.229
MOL File: 13860-38-3.mol

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1-methylpseudouridine Property

Density: 1.576±0.06 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: >20 mg/mL in EtOH; >20.65 mg/mL in DMSO
pka: 9.43±0.10(Predicted)
form: A solid
color: White to off-white
Water Solubility: insoluble in Water;
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)/t5-,6-,7-,8+/s3
InChIKey: UVBYMVOUBXYSFV-CAYFCZNJNA-N
SMILES: [C@@H]1(O)[C@@H](CO)O[C@@H](C2C(=O)NC(=O)N(C)C=2)[C@@H]1O |&1:0,2,6,16,r|

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SMB01360
Product name: 1-MethylpseudoUridine
Purity: ≥98% (HPLC)
Packaging: 50MG
Price: $124
Updated: 2024/03/01

Sigma-Aldrich

Product number: SMB01360
Product name: 1-MethylpseudoUridine
Purity: ≥98% (HPLC)
Packaging: 250MG
Price: $496
Updated: 2024/03/01

Usbiological

Product number: 296307
Product name: 1-Methylpseudouridine
Packaging: 1mg
Price: $347
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NM35520
Product name: 1-Methylpseudouridine
Packaging: 25mg
Price: $475
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NM35520
Product name: 1-Methylpseudouridine
Packaging: 0.5g
Price: $571
Updated: 2021/12/16

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1-methylpseudouridine Chemical Properties,Usage,Production

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).

Biochem/physiol Actions

N1-methylpseudouridine (m1Ψ), the modification used in the current mRNA SARS-CoV-2 vaccines, was found to possess superior characteristics to Ψ; m1Ψ elicited less immunogenicity and increased protein production by more than an order of magnitude relative to Ψ m1Ψ preserves the fidelity of tRNA selection by the ribosome. Kim et al. explored the effect of m1Ψ and Ψ on decoding using various in vitro systems. They found that m1Ψ slightly decreases the rate of peptide-bond formation. It also suppresses near-stop codon recognition by release factors and m1Ψ-modified SARS-CoV-2 spike protein mRNA is translated faithfully by eukaryotic ribosomes. Unlike Ψ, m1Ψ does not stabilize mismatches during RNA-duplex formation. Ψ, but not m1Ψ, increases errors by reverse transcriptases[3].

Advantages

N1-Methylpseudouridine is the methylated derivative of pseudouridine. It is used in in vitro transcription and for the production of RNA vaccines.In vertebrates, it stimulates significantly less activation of the innate immune response compared to uridine,while the translation is stronger.In protein biosynthesis, it is read like uridine and enables comparatively high protein yields.The nucleoside itself can be made by chemical methylation of pseudouridine.

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.
3. Kyusik Q Kim. “N1-methylpseudouridine found within COVID-19 mRNA vaccines produces faithful protein products.” Cell reports 40 9 (2022): 111300.

1-methylpseudouridine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 1-methylpseudouridine manufacturers

Hefei Huana Biomedical Technology Co.,Ltd.

Product: 1-Methylpseudouridine 13860-38-3
Price: US $0.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 100kg
Release date: 2023-05-09

Yunbio Tech Co.,Ltd.

Product: N1-Methylpseudouridine 13860-38-3
Price: US $0.00-0.00/g
Min. Order: 10g
Purity: 99.5%
Supply Ability: 100kg monthly
Release date: 2022-02-24

Henan Fengda Chemical Co., Ltd

Product: 1-methylpseudouridine 13860-38-3
Price: US $8.00-6.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-04-23

13860-38-3, 1-methylpseudouridineRelated Search:

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1-methylpseudouridine

(-)-1-Methyl-5-(β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione

1-Methyl-5-(β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione

1-Methyl-5-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione

Antibiotic U-50228

U-50228

N1-Methylpseudouridine

1-N-ME-PSEUDOURIDINE

N1-methyl-Pseudo-UTP.3Na 100mM solution

N1-Me-Pseudouridine

2,4(1H,3H)-Pyrimidinedione,1-methyl-5-b-D-ribofuranosyl-

5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-methylpyrimidine-2,4(1H,3H)-dione

N1-Methylpseudouridine RNA-modified nucleoside m1Y

N1-Me-Pseudouridine/N1-Methyl-Pseudouridine

Beta-1-Methylpseudouridine

N1-methylpseudourine

GFP,Inhibitor,mRNA,inhibit,DNA/RNA Synthesis,N1-Methylpseudouridine,eIF2α,Nucleoside Antimetabolite/Analog,phosphorylation,protein,expression,N1 Methylpseudouridine,N-1-Methylpseudouridine,cells,HEK293T,polysomes,ribosome,N1Methylpseudouridine

Nl-methylpseudourine

2,4(1H,3H)-Pyrimidinedione, 1-methyl-5-β-D-ribofuranosyl-

1-Methyipseudouridine

1-Methyl pseudouridine (m1ψ)

1-Methyl-5-beta-D-ribofuranosyl-1H-pyrimidine-2,4-dione

N1-methylpeudouridine

N1-Methyl-2'-O-TBDMS-pseudouridine

13860-38-3

Pharmaceutical

Nucleotides

Nucleosides

Nucleosides-Pseudouridine Nucleosides