75759-66-9

Upstream product

• 957-75-5 5-bromouridine 
• 98-80-6 phenylboronic acid 
• 869880-87-5 5-bromo-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene uridine 
• 1024-99-3 5-iodouridine 
• 1311164-92-7 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-5-phenyluridine 
• 71-43-2 benzene 
• 19556-58-2 5-iodo-2',3'-O isopropylidene-uridine 
• 75759-65-8 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

5-Phenyl-uridine trihydrate

In the title compound, C15H16N2O 6·~3H2O, the substituted uracil ring is oriented in the anti position relative to the ribose ring, and the phenyl and uracil rings are oriented in a noncoplanar fashion. The furanose ring adopts a conformation close to 3′-endo, in contrast to the furanose conformation seen in the crystal structure of the synthetic precursor 5-bromo-uridine, which is close to 2′-endo. The mol-ecule is involved in an extensive hydrogen-bonding network with several water mol-ecules, some of which are disordered.

Analogues of uracil nucleosides with intrinsic fluorescence (NIF-analogues): Synthesis and photophysical properties

Uridine cannot be utilized as fluorescent probe due to its extremely low quantum yield. For improving the uracil fluorescence characteristics we extended the natural chromophore at the C5 position by coupling substituted aromatic rings directly or via an alkenyl or alkynyl linker to create fluorophores. Extension of the uracil base was achieved by treating 5-I-uridine with the appropriate boronic acid under the Suzuki coupling conditions. Analogues containing an alkynyl linker were obtained from 5-I-uridine and the suitable boronic acid in a Sonogashira coupling reaction. The uracil fluorescent analogues proposed here were designed to satisfy the following requirements: a minimal chemical modification at a position not involved in base-pairing, resulting in relatively long absorption and emission wavelengths and high quantum yield. 5-((4-Methoxy-phenyl)-trans-vinyl)-2′-deoxy-uridine, 6b, was found to be a promising fluorescent probe. Probe 6b exhibits a quantum yield that is 3000-fold larger than that of the natural chromophore (Φ 0.12), maximum emission (478 nm) which is 170 nm red shifted as compared to uridine, and a Stokes shift of 143 nm. In addition, since probe 6b adopts the anti conformation and S sugar puckering favored by B-DNA, it makes a promising nucleoside analogue to be incorporated in an oligonucleotide probe for detection of genetic material.

Practical synthesis of 6-aryluridines via palladium(II) acetate catalyzed Suzuki-Miyaura cross-coupling reaction

Sugar-protected 6-halouridine derivatives underwent Suzuki-Miyaura cross-coupling reactions with arylboronic acids in the presence of palladium(II) acetate as a catalyst, triphenylphosphine as a ligand, and sodium carbonate as a base. This methodology is

Novel derivatives of UDP-glucose: Concise synthesis and fluorescent properties

A series of novel 5-substituted UDP-glucose derivatives with interesting fluorescent properties and potential applications as sensors for carbohydrate-active enzymes is reported. An efficient synthesis of the target molecules was developed, centred around the Suzuki-Miyaura reaction of (hetero)arylboronic acids with 5-iodo UDP-glucose. Interestingly, the optimised cross-coupling conditions could also be applied successfully to 5-bromo UMP, but not to 5-bromo UDP-glucose. The Royal Society of Chemistry.

A SIMPLE SYNTHESIS OF FLUORESCENT URIDINES BY PHOTOCHEMICAL METHOD

A strongly fluorescent 5-pyrenyluridine was prepared by the photoreaction of 2',3'-O-isopropylidene-5-iodouridine with pyrene.Several fluorescent analogues of uracil were synthesized by similar procedures.