MedKoo Cat#: 122471 | Name: 5-Methoxyuridine
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Description:

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

5-Methoxyuridine is an intermediate in the biosynthesis of pyrimidines and is also used as a precursor for other compounds.

Chemical Structure

5-Methoxyuridine
5-Methoxyuridine
CAS#35542-01-9

Theoretical Analysis

MedKoo Cat#: 122471

Name: 5-Methoxyuridine

CAS#: 35542-01-9

Chemical Formula: C10H14N2O7

Exact Mass: 274.0801

Molecular Weight: 274.23

Elemental Analysis: C, 43.80; H, 5.15; N, 10.22; O, 40.84

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 Weeks
1g USD 550.00 2 Weeks
5g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
5-Methoxyuridine; Uridine, 5-methoxy-; mo(5)u
IUPAC/Chemical Name
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methoxypyrimidine-2,4(1H,3H)-dione
InChi Key
ZXIATBNUWJBBGT-JXOAFFINSA-N
InChi Code
InChI=1S/C10H14N2O7/c1-18-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)19-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
SMILES Code
OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N(C(N2)=O)C=C(OC)C2=O)O1
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 274.23 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
1: Wang C, Zhang Y, Dong Y. Lipid Nanoparticle-mRNA Formulations for Therapeutic Applications. Acc Chem Res. 2021 Dec 7;54(23):4283-4293. doi: 10.1021/acs.accounts.1c00550. Epub 2021 Nov 18. PMID: 34793124. 2: Vaidyanathan S, Azizian KT, Haque AKMA, Henderson JM, Hendel A, Shore S, Antony JS, Hogrefe RI, Kormann MSD, Porteus MH, McCaffrey AP. Uridine Depletion and Chemical Modification Increase Cas9 mRNA Activity and Reduce Immunogenicity without HPLC Purification. Mol Ther Nucleic Acids. 2018 Sep 7;12:530-542. doi: 10.1016/j.omtn.2018.06.010. Epub 2018 Jun 30. PMID: 30195789; PMCID: PMC6076213. 3: Murao K, Ishikura H, Albani M, Kersten H. On the biosynthesis of 5-methoxyuridine and uridine-5-oxyacetic acid in specific procaryotic transfer RNAs. Nucleic Acids Res. 1978 Apr;5(4):1273-81. doi: 10.1093/nar/5.4.1273. PMID: 418384; PMCID: PMC342075. 4: Murao K, Hasegawa T, Ishikura H. 5-methoxyuridine: a new minor constituent located in the first position of the anticodon of tRNAAla, tRNAThr, and tRNAVal from Bacillus subtilis. Nucleic Acids Res. 1976 Oct;3(10):2851-60. doi: 10.1093/nar/3.10.2851. PMID: 825836; PMCID: PMC343132. 5: Ryu H, Grove TL, Almo SC, Kim J. Identification of a novel tRNA wobble uridine modifying activity in the biosynthesis of 5-methoxyuridine. Nucleic Acids Res. 2018 Sep 28;46(17):9160-9169. doi: 10.1093/nar/gky592. PMID: 29982645; PMCID: PMC6158493. 6: Shibaev VK, Eliseeva GI, Kochetkov NK. Sntez 5-aminouridin-5'-fosfata i 5-metoksiuridin-5'-fosfata [Synthesis of 5-aminouridine-5'-phosphate and 5-methoxyuridine-5'-phosphate]. Dokl Akad Nauk SSSR. 1972 Apr 1;203(4):860-2. Russian. PMID: 5024692. 7: Lauhon CT. Identification and Characterization of Genes Required for 5-Hydroxyuridine Synthesis in Bacillus subtilis and Escherichia coli tRNA. J Bacteriol. 2019 Sep 20;201(20):e00433-19. doi: 10.1128/JB.00433-19. PMID: 31358606; PMCID: PMC6755726. 8: Albani M, Schmidt W, Kersten H, Geibel K, Lüderwald I. 5-Methoxyuridine, a new modified constituent in tRNAs of Bacillaceae. FEBS Lett. 1976 Nov;70(1):37-42. doi: 10.1016/0014-5793(76)80721-1. PMID: 825391. 9: Rafehi M, Müller CE. Tools and drugs for uracil nucleotide-activated P2Y receptors. Pharmacol Ther. 2018 Oct;190:24-80. doi: 10.1016/j.pharmthera.2018.04.002. Epub 2018 Apr 13. PMID: 29660366. 10: Li B, Luo X, Dong Y. Effects of Chemically Modified Messenger RNA on Protein Expression. Bioconjug Chem. 2016 Mar 16;27(3):849-53. doi: 10.1021/acs.bioconjchem.6b00090. Epub 2016 Mar 4. PMID: 26906521. 11: 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. 12: Nasvall SJ, Chen P, Bjork GR. The modified wobble nucleoside uridine-5-oxyacetic acid in tRNAPro(cmo5UGG) promotes reading of all four proline codons in vivo. RNA. 2004 Oct;10(10):1662-73. doi: 10.1261/rna.7106404. PMID: 15383682; PMCID: PMC1370651. 13: Takai K, Okumura S, Hosono K, Yokoyama S, Takaku H. A single uridine modification at the wobble position of an artificial tRNA enhances wobbling in an Escherichia coli cell-free translation system. FEBS Lett. 1999 Mar 19;447(1):1-4. doi: 10.1016/s0014-5793(99)00255-0. PMID: 10218569. 14: Yamada Y, Matsugi J, Ishikura H, Murao K. Bacillus subtilis tRNA(Pro) with the anticodon mo5UGG can recognize the codon CCC. Biochim Biophys Acta. 2005 May 1;1728(3):143-9. doi: 10.1016/j.bbaexp.2005.02.011. Epub 2005 Mar 22. PMID: 15833716. 15: Sheng J, Zhang W, Hassan AE, Gan J, Soares AS, Geng S, Ren Y, Huang Z. Hydrogen bond formation between the naturally modified nucleobase and phosphate backbone. Nucleic Acids Res. 2012 Sep;40(16):8111-8. doi: 10.1093/nar/gks426. Epub 2012 May 28. PMID: 22641848; PMCID: PMC3439885. 16: Matsugi J, Jia HT, Murao K, Ishikura H. Nucleotide sequences of serine tRNAs from Bacillus subtilis. Biochim Biophys Acta. 1992 Apr 6;1130(3):333-5. doi: 10.1016/0167-4781(92)90448-9. PMID: 1373329. 17: Masuda I, Takase R, Matsubara R, Paulines MJ, Gamper H, Limbach PA, Hou YM. Selective terminal methylation of a tRNA wobble base. Nucleic Acids Res. 2018 Apr 20;46(7):e37. doi: 10.1093/nar/gky013. PMID: 29361055; PMCID: PMC5909439. 18: Jiang T, Henderson JM, Coote K, Cheng Y, Valley HC, Zhang XO, Wang Q, Rhym LH, Cao Y, Newby GA, Bihler H, Mense M, Weng Z, Anderson DG, McCaffrey AP, Liu DR, Xue W. Chemical modifications of adenine base editor mRNA and guide RNA expand its application scope. Nat Commun. 2020 Apr 24;11(1):1979. doi: 10.1038/s41467-020-15892-8. PMID: 32332735; PMCID: PMC7181807. 19: Okumura S, Takai K, Yokoyama S, Takaku H. Codon recognition by tRNA molecules with a modified or unmodified uridine at the first position of the anticodon. Nucleic Acids Symp Ser. 1995;(34):203-4. PMID: 8841623. 20: Hasegawa T, Murao K, Ishikura H. The nucleotide sequence of proline tRNAmo5UGG from Bacillus subtilis. Biochem Int. 1985 Apr;10(4):663-71. PMID: 3927921.