Westphal Reaction in Solid-Phase

Delgado, Francisco; Linares, Manuel; Alajarı́n, Ramón; Vaquero, Juan J.; Alvárez‐Builla, Julio

doi:10.1021/ol035417z

Cited by 15 publications

(14 citation statements)

References 23 publications

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“…Et 3 N (0.26 mL, 1.86 mmol, 1 eq) was added to a stirred solution of 4-[( E )-2-(acetylphenylamino)ethenyl]-1-methylquinolinium iodide 28 (790 mg, 1.84 mmol, 1 eq) and 2-(2-methylbenz[ d ]oxazole-3-ium-3-yl) acetate 42 (500 mg, 2.62 mmol, 1.42 eq) in DCM. The solution was left to stir for 20 h followed by in vacuo concentration.…”

Section: Methodsmentioning

confidence: 99%

Development of a genetically encodable FRET system using fluorescent RNA aptamers

et al. 2018

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Fluorescent RNA aptamers are useful as markers for tracking RNA molecules inside cells and for creating biosensor devices. Förster resonance energy transfer (FRET) based on fluorescent proteins has been used to detect conformational changes, however, such FRET devices have not yet been produced using fluorescent RNA aptamers. Here we develop an RNA aptamer-based FRET (apta-FRET) system using single-stranded RNA origami scaffolds. To obtain FRET, the fluorescent aptamers Spinach and Mango are placed in close proximity on the RNA scaffolds and a new fluorophore is synthesized to increase spectral overlap. RNA devices that respond to conformational changes are developed, and finally, apta-FRET constructs are expressed in E. coli where FRET is observed, demonstrating that the apta-FRET system is genetically encodable and that the RNA nanostructures fold correctly in bacteria. We anticipate that the RNA apta-FRET system could have applications as ratiometric sensors for real-time studies in cell and synthetic biology.

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Section: Methodsmentioning

confidence: 99%

Development of a genetically encodable FRET system using fluorescent RNA aptamers

et al. 2018

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“…The bisaldehyde 2 was prepared in 49 % yield through the nucleophilic reaction of 4-(diethylamino)-2-hydroxybenzaldehyde 1 with 1,3-dibromopropane in the presence of K 2 CO 3 . Subsequent reaction of 2 with 2,3-dimethyldehydroquinolizinium chloride [48] in ethanol in the presence of piperidine as a catalyst yielded the bisstyryldehydropyridocolinium derivative. The anions were exchanged by stirring the reaction mixture with excess KBF 4 in ethanol solution.…”

Section: Resultsmentioning

confidence: 99%

A Novel Styryldehydropyridocolinium Homodimer: Synthesis and Fluorescence Properties Upon Interaction with DNA

et al. 2015

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A novel homodimer of the styryldehydropyridocolinium dye (TPTP) has been synthesized and characterized. Free TPTP exhibited low fluorescence quantum yield and large Stokes shift (over 160 nm) in water. However, it showed a significant fluorescence turn-on effect upon intercalation into DNA base pairs. Meanwhile, the fluorescence intensity of the intercalated structures formed by TPTP and DNA decreased quickly upon addition of deoxyribonuclease I, indicating that the dye can be used to monitor deoxyribonuclease I activity and DNA hydrolysis. Electrophoresis analysis revealed that the dye had intercalative binding to DNA and can potentially be used for DNA staining in electrophoresis. Thus, the innate nature of large Stokes shift and excellent fluorescence turn on effect upon interaction with DNA endue the dye with a wide range of applications.

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“…Alvarez‐Builla et al developed a solid‐phase Westphal reaction for 1,4‐dinucleophile azinium or azolium salts (C‐C substrates) and a library of nitrogen bridgehead cycloimmonium salts has been prepared in high yields (Scheme ) . By reaction of solid‐support‐bound azolium or azinium acetates ( 219 or 222 ), 1,2‐diketones 223 , and base, cycloimmonium salts 224 were synthesized in good to high yields and purities.…”

Section: Synthetic Approaches Towards Azatriphenylene Derivatives:mentioning

confidence: 99%

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

et al. 2018

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This review surveys the most useful strategies for the synthesis of azatriphenylenes. Azatriphenylene derivatives are of considerable interest due to their promising photophysical and coordinating properties and to their presence in the composition of natural products. These scaffolds have shown ability as photoluminescent chemosensors for organic anions and nitroaromatic compounds. The straight‐forward construction of an azatriphenylene moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry and material sciences. These target compounds can also be used as components of (metallo)intercalators (insertors) for biological studies as well as photoluminescent emitters. Here we report a review on the synthesis of these scaffolds employing different strategies such as cyclocondensation reaction, Friedel–Crafts reaction, Westphal condensation reaction, Chichibabin‐type condensation reaction, coupling reaction, intermolecular homocoupling‐cyclotrimerization reaction, cycloaddition reaction, Pomeranz–Fritsch cyclization and intramolecular cyclization reaction. In addition, a brief historical approach has also been discussed. This review will cover the synthetic routes to afford azatriphenylene derivatives broadly including mono‐, di‐, tri‐, tetra, and hexa‐azatriphenylenes. As a consequence, this review will contribute ample and updated information on the synthesis of this class of compounds.

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Westphal Reaction in Solid-Phase

Abstract: [reaction: see text]. A library of cycloimonium salts has been prepared through Westphal reaction in solid-phase. By reaction of solid-support-bound azolium or azinium acetates 2, 1,2-diketones 4, and base, cycloimonium salts 5 were synthesized in good to high yield and purities.

Cited by 15 publications

References 23 publications

Development of a genetically encodable FRET system using fluorescent RNA aptamers

Development of a genetically encodable FRET system using fluorescent RNA aptamers

A Novel Styryldehydropyridocolinium Homodimer: Synthesis and Fluorescence Properties Upon Interaction with DNA

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

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