Sequential conjugation methods based on triazole formation and related reactions using azides

Yoshida, Suguru

doi:10.1039/c9ob02698c

Cited by 29 publications

(8 citation statements)

References 127 publications

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“…9 Generally, desired oligotriazoles can be prepared from various platform compounds bearing two or more clickable units (presence of two or more azide/alkyne unit) and triazoles were formed using a sequential conjugation strategy. 10 It was possible to react one particular molecule bearing two or more alkyne moieties selectively, with an organic azide by using a temporary masking group such as trialkylsilyl group. 11 However, platform molecules, such as diynes, diazides, triynes, and triazides containing either azido and alkyne component may lead to the generation of multitriazoles.…”

Section: Oligotriazoles Connected By Situable Building Blockmentioning

confidence: 99%

“…11 However, platform molecules, such as diynes, diazides, triynes, and triazides containing either azido and alkyne component may lead to the generation of multitriazoles. 10 In presence of anion, oligomers were shown to fold into ordered conformations in solution via non covalent interactions and resulted in the formation of anion templated foldamer, an interesting chemical entity. 12 A wide spectrum of potential applications are expected for oligo-1,2,3-triazole-based functional materials, such as supermolecules, fluorescence probes, and biological proteins.…”

Section: Oligotriazoles Connected By Situable Building Blockmentioning

confidence: 99%

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“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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A typical 1,2,3-triazoles are important aromatic heterocyclic compounds with three adjacent nitrogen atoms. These "unnatural" heterocycles found applications in pharmaceutical science, material science and chemical biology. Oligo-1,2,3-triazole linked molecules showed interesting applications in the field of DNA binding, selfassembly, surface modification, supramolecular chemistry etc. In this article, oligo-1,2,3-triazoles are broadly classified into two categories: (i) 1,2,3-triazoles are connected through varieties of organic molecules and (ii) triazole units are connected with one another either by N-(CH)n-C linkages or by amide bonds generated from amino acids. Syntheses and properties of some of these oligomers are reviewed in this article.

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Section: Oligotriazoles Connected By Situable Building Blockmentioning

confidence: 99%

Section: Oligotriazoles Connected By Situable Building Blockmentioning

confidence: 99%

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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“…92,103,105 The nonhydrolysis Staudinger ligation is also compatible with other bioorthogonal reactions. 112 Mutually orthogonal bioorthogonal chemistries are desirable for multicomponent labeling studies. However, only a handful of such reactions can be used in tandem.…”

Section: Staudinger Ligationmentioning

confidence: 99%

Bioorthogonal Reactions of Triarylphosphines and Related Analogues

2021

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Bioorthogonal phosphines were introduced in the context of the Staudinger ligation over 20 years ago. Since that time, phosphine probes have been used in myriad applications to tag azide-functionalized biomolecules. The Staudinger ligation also paved the way for the development of other phosphorus-based chemistries, many of which are widely employed in biological experiments. Several reviews have highlighted early achievements in the design and application of bioorthogonal phosphines. This review summarizes more recent advances in the field. We discuss innovations in classic Staudinger-like transformations that have enabled new biological pursuits. We also highlight relative newcomers to the bioorthogonal stage, including the cyclopropenone-phosphine ligation and the phospha-Michael reaction. The review concludes with chemoselective reactions involving phosphite and phosphonite ligations. For each transformation, we describe the overall mechanism and scope. We also showcase efforts to fine-tune the reagents for specific functions. We further describe recent applications of the chemistries in biological settings. Collectively, these examples underscore the versatility and breadth of bioorthogonal phosphine reagents.

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“…At the beginning of the XXI century, in 2002, a group of scientists led by Rostovtsev et al and Tornoe et al discovered that the cycloaddition of terminal alkynes and organic azides in the presence of a catalyst of copper (I) salts forms only one 1,4isomer [8,9,16,17]. In this reaction, the function of the Cu(I) salt and the related mechanism were fully justified.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2,3-triazole derivatives based on propargyl ester of a saturated single-basic carbonic acid and para-azidobenzoic acid

Azizovich

Bakhtiyarovich²,

Sobirovich

2021

Eur J Chem

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The development of highly effective and low-toxicity nonsteroidal anti-inflammatory drugs (NSAIDs) is one of the important challenges facing modern pharmacology. To overcome this problem, many studies have been conducted on compounds containing a five-membered heterocycle containing three nitrogen atoms. The pharmacodynamics of these compounds are mainly due to their anti-inflammatory effect. Therefore, it is important to synthesize new derivatives of 1,2,3-triazoles, to determine their structure and to look for substances with anti-inflammatory activity on their basis. For the first time, the corresponding derivatives of 4-(4-(exchangeable)-1H-1,2,3-triazole-1-yl)-benzoic acid were synthesized by cycloaddition of propargyl esters of saturated carboxylic acids and para-azidobenzoic acid in the presence of copper (I) iodide. The structure of the obtained substances was analyzed by IR, 1H NMR, and MS techniques. It is proved that under the action of the catalyst in the reaction, only 1,4-isomers are formed. Factors affecting the course of the reaction were identified. Only one isomer is formed in the reaction of cyclic addition under the action of a catalyst and the effect of temperature, duration of time, and nature of the solvent on the reaction yield was studied.

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Sequential conjugation methods based on triazole formation and related reactions using azides

Abstract: This review highlights recent transformations involving selective triazole formation, allowing efficient preparation of unsymmetric bis- and tris(triazole)s using diverse platform molecules.

Cited by 29 publications

References 127 publications

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Bioorthogonal Reactions of Triarylphosphines and Related Analogues

Synthesis of 1,2,3-triazole derivatives based on propargyl ester of a saturated single-basic carbonic acid and para-azidobenzoic acid

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