29428-50-0

Usage

Uses

Used in Molecular Biology:
5-Pyrimidineacetic acid, 1,2,3,4-tetrahydro-2,4-dioxo-1-beta-D-ribofuranosyl-, methyl ester is used as a structural component for enhancing the stability and functionality of transfer RNA in yeast. Its presence in the transfer RNA molecule contributes to the accurate translation of genetic information during protein synthesis.
Used in Pharmaceutical Research:
As a derivative of uridine, 5-Pyrimidineacetic acid, 1,2,3,4-tetrahydro-2,4-dioxo-1-beta-D-ribofuranosyl-, methyl ester may have potential applications in the development of novel therapeutic agents targeting RNA-related diseases or conditions. Its unique structure could be exploited for designing drugs that modulate RNA function or interact with specific RNA targets.
Used in Biochemical Studies:
5-Pyrimidineacetic acid, 1,2,3,4-tetrahydro-2,4-dioxo-1-beta-D-ribofur anosyl-, methyl ester can be utilized in biochemical research to investigate the role of modified nucleosides in RNA biology, gene expression, and cellular processes. Understanding the function and importance of such modifications can provide insights into the molecular mechanisms underlying various biological phenomena and may lead to the discovery of new targets for therapeutic intervention.
Used in Synthetic Chemistry:
5-Pyrimidineacetic acid, 1,2,3,4-tetrahydro-2,4-dioxo-1-beta-D-ribofuranosyl-, methyl ester can serve as a starting material or intermediate in the synthesis of more complex nucleoside analogs and RNA derivatives. These synthesized compounds can be used for various applications, including the development of new drugs, imaging agents, or research tools.

InChI:InChI=1/C12H16N2O8/c1-21-7(16)2-5-3-14(12(20)13-10(5)19)11-9(18)8(17)6(4-15)22-11/h3,6,8-9,11,15,17-18H,2,4H2,1H3,(H,13,19,20)/t6-,8-,9-,11-/m1/s1

Upstream product

• 957-77-7 5-Hydroxy-uridin 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 67-56-1 methanol 
• 20964-06-1 5-(carboxymethyl)uridine 
• 110920-78-0 N³,5'-O-dibenzoyl-2',3'-O-isopropylideneuridine-5-malonic acid dimethyl ester 
• 54503-61-6 2',3'-O-isopropylidene-5-bromouridine 
• 1261157-40-7 N₃-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester 
• 20299-15-4 2-thio-5-<(methylcarboxy)methyl>uridine 
• 1261157-39-4 5-bromo-N3-benzoyl-2’,3’,5’-tri-O-acetyluridine 
• 105659-31-2 5-bromo-2’,3’,5’-tri-O-acetyluridine 
• 4105-38-8 Tri-O-acetyluridine 
• 58-96-8 uridine 
• 110920-77-9 N³,5'-O-dibenzoyl-5-bromo-2',3'-O-isopropylideneuridine 
• 159555-11-0 2,2'-anhydro-1-(β-D-arabinofuranosyl)-5-(methoxycarbonylmethyl)-uracil 

Downstream Products

• 321991-67-7 5'-O-(4,4'-dimethoxytrityl)-5-carbomethoxymethyluridine 
• 1261157-40-7 N₃-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester 
• 29569-30-0 5-(carbamoylmethyl)uridine 

Relevant academic research and scientific papers

Novel C-C Bond Formation at the 5-Position of Uracils. Facile Synthesis of 5-Methoxycarbonylmethyluridine and 5-Carbamoylmethyluridine, Minor Component Nucleosides derived from transfer Ribonuclease

5-Hydroxyuracil derivatives were treated with stable Wittig reagents to give the corresponding 5-alkyluracil derivatives such as 5-methoxycarbonylmethyluridine and 5-carbamoylmethyluridine.

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.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

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

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

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

MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF

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

The AlkB domain of mammalian ABH8 catalyzes hydroxylation of 5-methoxycarbonylmethyluridine at the wobble position of tRNA

Family ties: The AlkB family of nonheme iron, α-ketoglutarate (αKG)-dependent dioxygenases is involved in biological processes such as DNA/RNA repair and obesity. The AlkB domain of ABH8 is shown to catalyze the hydroxylation of a modified uridine (mcmsu

Efficient Synthesis of New 5-Substituted Uracil Nucleosides Useful for Linker Arm Incorporation

5-Substituted uracil nucleosides useful for the attachment of linker arms to nucleic acids are prepared from arabinoaminooxazoline and dimethyl α-bromomethylfumarate in a short reaction sequence without using any protecting groups, and incorporated into o

Chemistry and structure of modified uridines in the anticodon, wobble position of transfer RNA are determined by thiolation

Uridines found in the first or wobble position of transfer RNA anticodons are most often modified at base ring carbon-5 and many times also thiolated at carbon-2. It is important to understand the chemistry and structure of the modified uridines because t

Reaction of 5-Bromouridine Derivatives with Dimethyl Malonate Carbanion. A Novel Entry to the Synthesis of Uridine-5-acetic Acids

The reaction of N3,5'-O-dibenzoyl-2',3'-O-isopropylidene-5-bromouridine (1) with dimethyl malonate in the presence of 1,8-diazabicycloundec-7-ene afforded a 5-malonate ester derivative (2) in high yield.Uridine-5-acetic acid (7) and its