MedKoo Cat#: 122469 | Name: Beta-1-Methylpseudouridine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Also known as 1-methylpseudouridine, is a methylpseudouridine in which the methyl group is located at position N-1 on the uracil ring.

Chemical Structure

Beta-1-Methylpseudouridine
CAS#13860-38-3

Theoretical Analysis

MedKoo Cat#: 122469

Name: Beta-1-Methylpseudouridine

CAS#: 13860-38-3

Chemical Formula: C10H14N2O6

Exact Mass: 258.0852

Molecular Weight: 258.23

Elemental Analysis: C, 46.51; H, 5.46; N, 10.85; O, 37.17

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
1-Methylpseudouridine; N1-Methylpseudouridine; N1-methyl-pseudouridine; NSC240023; NSC 240023; NSC-240023; U-50228; U50228; U 50228
IUPAC/Chemical Name
5-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-methylpyrimidine-2,4(1H,3H)-dione
InChi Key
UVBYMVOUBXYSFV-WCTZXXKLSA-N
InChi Code
InChI=1S/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-/m1/s1
SMILES Code
O[C@H]1[C@@H](O)[C@@H](C2=CN(C)C(NC2=O)=O)O[C@@H]1CO
Appearance
To be determined
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 258.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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PMID: 34793124. 4: Pardi N, Tuyishime S, Muramatsu H, Kariko K, Mui BL, Tam YK, Madden TD, Hope MJ, Weissman D. Expression kinetics of nucleoside-modified mRNA delivered in lipid nanoparticles to mice by various routes. J Control Release. 2015 Nov 10;217:345-51. doi: 10.1016/j.jconrel.2015.08.007. Epub 2015 Aug 8. PMID: 26264835; PMCID: PMC4624045. 5: Mokuda S, Watanabe H, Kohno H, Ishitoku M, Araki K, Hirata S, Sugiyama E. N1-methylpseudouridine-incorporated mRNA enhances exogenous protein expression and suppresses immunogenicity in primary human fibroblast-like synoviocytes. Cytotechnology. 2022 Aug;74(4):503-514. doi: 10.1007/s10616-022-00540-4. Epub 2022 Jun 30. PMID: 35791402; PMCID: PMC9245880. 6: Baiersdörfer M, Boros G, Muramatsu H, Mahiny A, Vlatkovic I, Sahin U, Karikó K. A Facile Method for the Removal of dsRNA Contaminant from In Vitro- Transcribed mRNA. Mol Ther Nucleic Acids. 2019 Apr 15;15:26-35. doi: 10.1016/j.omtn.2019.02.018. Epub 2019 Feb 27. PMID: 30933724; PMCID: PMC6444222. 7: Parr CJC, Wada S, Kotake K, Kameda S, Matsuura S, Sakashita S, Park S, Sugiyama H, Kuang Y, Saito H. N 1-Methylpseudouridine substitution enhances the performance of synthetic mRNA switches in cells. Nucleic Acids Res. 2020 Apr 6;48(6):e35. doi: 10.1093/nar/gkaa070. PMID: 32090264; PMCID: PMC7102939. 8: Hoehn SJ, Krul SE, Skory BJ, Crespo-Hernández CE. Increased Photostability of the Integral mRNA Vaccine Component N1 -Methylpseudouridine Compared to Uridine. Chemistry. 2022 Jan 27;28(6):e202103667. doi: 10.1002/chem.202103667. Epub 2021 Dec 21. PMID: 34875113. 9: Sample PJ, Wang B, Reid DW, Presnyak V, McFadyen IJ, Morris DR, Seelig G. Human 5' UTR design and variant effect prediction from a massively parallel translation assay. Nat Biotechnol. 2019 Jul;37(7):803-809. doi: 10.1038/s41587-019-0164-5. Epub 2019 Jul 1. PMID: 31267113; PMCID: PMC7100133. 10: Argoudelis AD, Mizsak SA. 1-methylpseudouridine, a metabolite of Streptomyces platensis. J Antibiot (Tokyo). 1976 Aug;29(8):818-23. doi: 10.7164/antibiotics.29.818. PMID: 993120. 11: Pardi N, Weissman D. Nucleoside Modified mRNA Vaccines for Infectious Diseases. Methods Mol Biol. 2017;1499:109-121. doi: 10.1007/978-1-4939-6481-9_6. PMID: 27987145. 12: Svitkin YV, Cheng YM, Chakraborty T, Presnyak V, John M, Sonenberg N. N1-methyl-pseudouridine in mRNA enhances translation through eIF2α-dependent and independent mechanisms by increasing ribosome density. Nucleic Acids Res. 2017 Jun 2;45(10):6023-6036. doi: 10.1093/nar/gkx135. PMID: 28334758; PMCID: PMC5449617. 13: Pang H, Ihara M, Kuchino Y, Nishimura S, Gupta R, Woese CR, McCloskey JA. Structure of a modified nucleoside in archaebacterial tRNA which replaces ribosylthymine. 1-Methylpseudouridine. J Biol Chem. 1982 Apr 10;257(7):3589-92. PMID: 7061499. 14: Chatterjee K, Blaby IK, Thiaville PC, Majumder M, Grosjean H, Yuan YA, Gupta R, de Crécy-Lagard V. The archaeal COG1901/DUF358 SPOUT-methyltransferase members, together with pseudouridine synthase Pus10, catalyze the formation of 1-methylpseudouridine at position 54 of tRNA. RNA. 2012 Mar;18(3):421-33. doi: 10.1261/rna.030841.111. Epub 2012 Jan 24. PMID: 22274953; PMCID: PMC3285931. 15: Dutta N, Deb I, Sarzynska J, Lahiri A. Data-informed reparameterization of modified RNA and the effect of explicit water models: application to pseudouridine and derivatives. J Comput Aided Mol Des. 2022 Mar;36(3):205-224. doi: 10.1007/s10822-022-00447-4. Epub 2022 Mar 26. PMID: 35338419; PMCID: PMC8956458. 16: Shanmugasundaram M, Senthilvelan A, Kore AR. Gram-Scale Chemical Synthesis of Base-Modified Ribonucleoside-5'-O-Triphosphates. Curr Protoc Nucleic Acid Chem. 2016 Dec 1;67:13.15.1-13.15.10. doi: 10.1002/cpnc.20. PMID: 27911496. 17: Wolf EJ, Grünberg S, Dai N, Chen TH, Roy B, Yigit E, Corrêa IR. Human RNase 4 improves mRNA sequence characterization by LC-MS/MS. Nucleic Acids Res. 2022 Oct 14;50(18):e106. doi: 10.1093/nar/gkac632. PMID: 35871301; PMCID: PMC9561288. 18: Brand RC, Klootwijk J, Planta RJ, Maden BE. Biosynthesis of a hypermodified nucleotide in Saccharomyces carlsbergensis 17S and HeLa-cell 18S ribosomal ribonucleic acid. Biochem J. 1978 Jan 1;169(1):71-7. doi: 10.1042/bj1690071. PMID: 629754; PMCID: PMC1184195. 19: Zhang Y, Xi X, Yu H, Yang L, Lin J, Yang W, Liu J, Fan X, Xu Y. Chemically modified in-vitro-transcribed mRNA encoding thrombopoietin stimulates thrombopoiesis in mice. Mol Ther Nucleic Acids. 2022 Aug 13;29:657-671. doi: 10.1016/j.omtn.2022.08.017. PMID: 36090760; PMCID: PMC9440273. 20: Piccirilli JA, Moroney SE, Benner SA. A C-nucleotide base pair: methylpseudouridine-directed incorporation of formycin triphosphate into RNA catalyzed by T7 RNA polymerase. Biochemistry. 1991 Oct 22;30(42):10350-6. doi: 10.1021/bi00106a037. PMID: 1718418.