Electrochemical behaviour and redox reactivity of some 4-R-1,2,4-triazolin-3,5-diones

Alstanei, Ana-Maria; Hornoiu, Cristian; Aycard, Jean‐Pierre; Carles, Micheline; Volanschi, Elena

doi:10.1016/s0022-0728(02)01441-9

Cited by 12 publications

(17 citation statements)

References 17 publications

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“…To date, only a few studies have reported the electrochemical activation of urazoles, and all of them deal with the electrosynthesis of chemicals or the functionalization of electrode surfaces. − In this work, we explored the possibility of electrochemically activating Ph-Ur species in the presence of proteins such as a traceless Y-labeling method. We applied an appropriate electrochemical potential to activate the Ph-Ur dormant species in situ, on demand, without oxidizing the sensitive amino acids from the protein or the ligands linked to the Ph-Ur (Figure A).…”

Section: Introductionmentioning

confidence: 99%

“…To date, only a few studies have reported the electrochemical activation of urazoles, 23 and all of them deal with the electrosynthesis of chemicals or the functionalization of electrode surfaces. 24−26 In this work, we explored the possibility of electrochemically activating Ph-Ur species in the presence of proteins such as a traceless Y-labeling method.…”

Section: ■ Introductionmentioning

confidence: 99%

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Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling

et al. 2018

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The development of new bio-orthogonal ligation methods for the conjugation of native proteins is of particular importance in the field of chemical biology and biotherapies. In this work, we developed a traceless electrochemical method for protein bioconjugation. The electrochemically promoted tyrosine-click (e-Y-CLICK) allowed the chemoselective Y-modification of peptides and proteins with labeled urazoles. A low potential is applied in an electrochemical cell to activate urazole anchors in situ and on demand, without affecting the electroactive amino acids from the protein. The versatility of the electrosynthetic approach was shown on biologically relevant peptides and proteins such as oxytocin, angiotensin 2, serum bovine albumin, and epratuzumab. The fully conserved enzymatic activity of a glucose oxidase observed after e-Y-CLICK further highlights the softness of the method. The e-Y-CLICK protocols were successfully performed in pure aqueous buffers, without the need for co-solvents, scavenger or oxidizing chemicals, and should therefore significantly broaden the scope of bioconjugation.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling

et al. 2018

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“…As such, its applicability in the generation of more complex bioconjugates was demonstrated . Inspired by the high reactivity of diazodicarboxylate reagents toward substituted phenols, the redox-active cyclic diazodicarboxamide PTAD was developed for Tyr-specific bioconjugation reactions. Exposure of an equimolar mixture of N -acyl methyl amides of His, Trp, Ser, Cys, Lys, and Tyr revealed exclusive reactivity of Tyr, thereby revealing the chemoselectivity of the reaction for phenol residues .…”

Section: Bioconjugation Chemistrymentioning

confidence: 99%

Oxidation-Induced “One-Pot” Click Chemistry

et al. 2021

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Click chemistry has been established rapidly as one of the most valuable methods for the chemical transformation of complex molecules. Due to the rapid rates, clean conversions to the products, and compatibility of the reagents and reaction conditions even in complex settings, it has found applications in many molecule-oriented disciplines. From the vast landscape of click reactions, approaches have emerged in the past decade centered around oxidative processes to generate in situ highly reactive synthons from dormant functionalities. These approaches have led to some of the fastest click reactions know to date. Here, we review the various methods that can be used for such oxidation-induced “one-pot” click chemistry for the transformation of small molecules, materials, and biomolecules. A comprehensive overview is provided of oxidation conditions that induce a click reaction, and oxidation conditions are orthogonal to other click reactions so that sequential “click-oxidation-click” derivatization of molecules can be performed in one pot. Our review of the relevant literature shows that this strategy is emerging as a powerful approach for the preparation of high-performance materials and the generation of complex biomolecules. As such, we expect that oxidation-induced “one-pot” click chemistry will widen in scope substantially in the forthcoming years.

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“…17 Volanschi and coworkers have investigated the electrochemical behavior and redox reactivity of several 4-substituted 1,2,4-triazole-3,5-diones. 18 TADs have been used both as substrates and reagents in various organic reactions including [2+2] cycloadditions, 19 dehydrogenation, 20 electrophilic aromatic substitution, 21 condensation of dicarbonyl compounds, 22 and oxidation of alcohols to aldehydes and ketones. 16,23 The varied reactivity of TADs makes them interesting compounds, however, they can be difficult to prepare and purify.…”

Section: Figurementioning

confidence: 99%