35542-01-9

Basic information

• Product Name: 5-METHOXYURIDINE
• Synonyms: 5-METHOXYURIDINE;mo(5)U;Uridine, 5-methoxy-
• CAS NO: 35542-01-9
• Molecular Formula: C₁₀H₁₄N₂O₇
• Molecular Weight: 274.23
• EINECS: 252-609-8
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 35542-01-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.65g/cm³
• Refractive Index: 1.641
• Storage Temp.: −20°C
• PKA: 8?+-.0.10(Predicted)
• CAS DataBase Reference: 5-METHOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYURIDINE(35542-01-9)
• EPA Substance Registry System: 5-METHOXYURIDINE(35542-01-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 35542-01-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxyuridine is used as a reagent in the synthesis of 5-OMe-UDP, a potent and selective P2Y6-receptor agonist. This application is significant for the development of new drugs targeting specific receptors, potentially leading to novel treatments for various conditions.
Used in Research and Development:
As an analog of uridine, 5-Methoxyuridine is utilized in research and development for studying the mechanisms of mRNA production in bacteria. Its ability to inhibit mRNA synthesis makes it a valuable tool for understanding ribosomal function and the processes involved in gene expression.
Used in Chemical Synthesis:
5-Methoxyuridine serves as a precursor for the synthesis of other compounds, making it an essential component in the chemical industry. Its role as an intermediate in the biosynthesis of pyrimidines highlights its importance in the development of new chemical entities with potential applications in various fields.

InChI:InChI=1/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

Upstream product

• 15715-58-9 triethylamine carbonate 
• 5975-18-8 bis(tri-n-butylammonium) pyrophosphate 
• 30771-43-8 2-thio-5-methoxyuridine 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 37805-86-0 5-methoxyuridine 2',3',5'-tri-O-benzoate 

Relevant articles and documents

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

Methotrexate adjuvants to reduce toxicity and methods for using the same

Methods are provided for using methotrexate (MTX) active agents in which reduced host toxicity is observed. Aspects of the methods include administering to a subject an effective amount of an MTX active agent in conjunction with a MTX toxicity-reducing adjuvant, such as a 2,2′-anhydropyrimidine, a derivative thereof or a uridine phosphorylase inhibitor. Also provided are compositions and kits that find use in practicing embodiments of the invention. The methods and compositions find use in a variety of applications, including the treatment of a variety of different disease conditions.

Synthesis and structure-activity relationship of uracil nucleotide derivatives towards the identification of human P2Y6 receptor antagonists

P2Y6 receptor (P2Y6-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y6-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5′-α,β-methylene-diphosphonate, 16 and 23, or lack of 2′-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y6-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y6-R (IC50 112 μM) versus P2Y2/4-Rs. In summary, we have established a comprehensive SAR for hP2Y6-R ligands towards the development of hP2Y6-R antagonists.

The influence of the C5 substituent on the 2-thiouridine desulfuration pathway and the conformational analysis of the resulting 4-pyrimidinone products

In recent years, increasing attention has been focused on the posttranscriptional modifications present in transfer RNAs (tRNAs), which have been suggested to constitute another level of regulation of gene expression. The most representative among them are the 5-substituted 2-thiouridines (R5S2U), which are located in the wobble position of the anticodon and play a fundamental role in the tuning of the translation process. On the other hand, sulfur-containing biomolecules are the primary site for the attack of reactive oxygen species (ROS). We have previously demonstrated that under in vitro conditions that mimic oxidative stress in the cell, the S2U alone or bound to an RNA chain undergoes desulfuration to yield uridine and 4-pyrimidinone nucleoside (H2U) products. The reaction is pH- and concentration-dependent. In this study, for the first time, we demonstrate that the substituent at the C5 position of the 2-thiouracil ring of R5S2Us influences the desulfuration pathway, and thus the products ratio. As the substituent R changes, the amount of R5H2U increases in the order H- > CH3O- > CH3OC(O)CH2- > HOC(O)CH2NHCH2- ≈ CH3NHCH2-, and this effect is more pronounced at lower pH. The conformational analysis of the resulting R5H2U products indicates that independent of the nature of the R5 substituent, the R5H2U nucleosides predominantly adopt a C2′-endo sugar ring conformation, as opposed to the preferred C3′-endo conformation of the parent R5S2Us.

Alternative nucleic acid molecules and uses thereof

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.