30414-00-7

Usage

Uses

Used in Pharmaceutical Industry:
5-(Hydroxymethyl)uridine is used as a therapeutic agent for the treatment of mitochondrial disorders due to its potential role in improving mitochondrial function and energy metabolism in cells.
Used in Neuroprotection:
5-(Hydroxymethyl)uridine is used as a neuroprotective agent to protect neurons from damage and degeneration, potentially offering benefits in the treatment of neurodegenerative diseases.
Used in Research:
5-(Hydroxymethyl)uridine is used as a research tool to study RNA modification, biosynthesis, and its effects on cellular processes, contributing to a better understanding of its biological significance and potential applications.

InChI:InChI=1/C10H14N2O7/c13-2-4-1-12(10(18)11-8(4)17)9-7(16)6(15)5(3-14)19-9/h1,5-7,9,13-16H,2-3H2,(H,11,17,18)/t5-,6-,7-,9-/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 58-96-8 uridine 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 24751-68-6 O^2'_,O3'_,O5'-tribenzoyl-5-bromomethyl-uridine 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 3816-77-1 2',3'-O-isopropylidene-5-hydroxymethyl-uridine 

Downstream Products

• 1463-10-1 5-Methyluridine 
• 220895-39-6 acetic acid 3-acetoxy-2-acetoxymethyl-6-(1-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethoxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester 
• 158532-72-0 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine 
• 917482-59-8 5-t-butyldiphenylsilyloxymethyl-5'-O-t-butyldiphenylsilyluridine 2',3'-bisxanthate 
• 917482-60-1 5-t-butyldiphenylsilyloxymethyl-5'-O-t-butyldiphenylsilyl-2',3'-didehydro-2',3'-dideoxyuridine 
• 917482-58-7 5-t-butyldiphenylsilyloxymethyl-5'-O-t-butyldiphenylsilyluridine 

Relevant academic research and scientific papers

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.

Interstrand cross-link and bioconjugate formation in RNA from a modified nucleotide

RNA oligonucleotides containing a phenyl selenide derivative of 5-methyluridine were chemically synthesized by solid-phase synthesis. The phenyl selenide is rapidly converted to an electrophilic, allylic phenyl seleneate under mild oxidative conditions. The phenyl seleneate yields interstrand cross-links when part of a duplex and is useful for synthesizing oligonucleotide conjugates. Formation of the latter is illustrated by reaction of an oligonucleotide containing the phenyl selenide with amino acids in the presence of mild oxidant. The products formed are analogous to those observed in tRNA that are believed to be formed posttranslationally via a biosynthetic intermediate that is chemically homologous to the phenyl seleneate. (Chemical Equation Presented).

Alternative synthetic routes to 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine

Alternative syntheses for the nucleoside analogue 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine starting from 5-methyluridine and uridine are described.

Synthesis and antiviral activity of C-5 substituted analogues of d4T bearing methylamino- or methyldiamino-linker arms

A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4t analogues of 'different sizes'. Reactions of the 2',3'- didehydro-2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via substitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

Synthesis of 5-(2-amino-2-deoxy-β-D-glucopyranosyloxymethyl)-2'- deoxyuridine and its incorporation into oligothymidylates

The protected 5-(2-amino-2-deoxy-β-D-glucopyranosyloxymethyl)-2'- deoxyuridine phosphoramidite 15 has been prepared from uridine in 12 steps. When incorporated into oligodeoxyribonucleotides the novel nucleoside analog 5 leads to decreased binding affinit