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Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V.; Sharpless, K. Barry

doi:10.1002/1521-3757(20020715)114:14<2708::aid-ange2708>3.0.co;2-0

Cited by 2,494 publications

(1,070 citation statements)

References 5 publications

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“…Various alkyne-modified amino acids were treated under copper-catalyzed click conditions with 1-azidoferrocene (2) and 1,1'-diazidoferrocene (2') efficiently as reported by Sharpless et al [8] Variable-temperature NMR spectroscopic measurements of the bivalent conjugate 19 showed the possibility of weak intramolecular hydrogen bonding between the triazole protons and the nitrogen of the other triazole ring. The redox potential measurements of monovalent and divalent conjugates showed quasi-reversible cyclic voltammetry (CV) waves.…”

Section: Introductionmentioning

confidence: 99%

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Ganesh

Sudhir

Kundu

et al. 2011

Chemistry An Asian Journal

121

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Click chemistry has played a significant role as a rapid and versatile strategy for conjugating two molecular fragments under very mild reaction conditions. Introduction of ferrocene-derived triazole systems using click chemistry has attracted enormous interest in various fields due to its potential applications in electrochemical techniques for detection and sensing. The present discussion focuses on the synthesis of ferrocene-triazole and the importance of using a CuAAC reaction for such conjugation. Applications of ferrocene-based click reactions in conjugate chemistry, asymmetric catalysis, medicinal chemistry, host-guest interactions, and materials chemistry have been highlighted.

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Section: Introductionmentioning

confidence: 99%

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Ganesh

Sudhir

Kundu

et al. 2011

Chemistry An Asian Journal

121

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“…5,6 The surface reaction is quantitative and regioselective, exclusively yielding a single product at a single orientation. The chemistry is orthogonal to most typical organic transformations and thus is chemoselective.…”

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confidence: 99%

Chemoselective Covalent Coupling of Oligonucleotide Probes to Self-Assembled Monolayers

et al. 2005

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Surface arrays of single-stranded DNA are at the center of some of the most active areas in biological research. These include conventional applications in genome sequencing and disease diagnostics, as well as more novel emerging examples, such as combinatorial drug and reaction discovery. 1 Most methods of oligonucleotide immobilization rely on traditional nucleophilicelectrophilic reactions to achieve coupling of the oligonucleotide to the surface. 2 Unfortunately, this strategy is susceptible to side reactions, for instance, with amino groups on the nucleotides or the small molecule contaminants inherent to oligonucleotide synthesis. 3 Additionally, popular reactive electrophiles, such as N-hydroxysuccinimide esters, are prone to hydrolysis before and during the coupling reaction, which both reduce coupling yields and can make the yields irreproducible. 4 Accurate and reproducible detection of target oligonucleotides depends on the accuracy and reproducibility with which the surface can be functionalized. In this paper, we report a chemoselective approach to the formation of oligonucleotide probe surfaces using copper(I) tris(benzyltriazolylmethyl)amine (TBTA)-catalyzed triazole formation between a controlled density of azide groups on densely packed selfassembled monolayers (SAMs) and acetylene groups on the oligonucleotide probe to be immobilized. We have found this strategy to be highly predictable, very fast, and resistant to side reactions, unaffected even by the presence of excess nucleophilic or electrophilic impurities.Recently, we have demonstrated that Sharpless "click" chemistry can be used to covalently attach acetylene-bearing molecules to azide-terminated SAMs. 5,6 The surface reaction is quantitative and regioselective, exclusively yielding a single product at a single orientation. The chemistry is orthogonal to most typical organic transformations and thus is chemoselective. 7 Recent studies have demonstrated that the chemistry is well suited for the coupling of biomolecules to surfaces. 8 Although application of this chemistry to the attachment of oligonucleotides may appear straightforward, the majority of past work used free Cu(I), typically generated and maintained in aqueous solution by an excess of reducing agent. Unfortunately, in the presence of dioxygen, Cu(I) rapidly damages DNA via the generation of reactive oxygen species. 9 In order for a surface array of oligonucleotides to be useful as a sensor, the structure of the oligonucleotides must be preserved. Recently, the Sharpless group has introduced a triazolylamine copper ligand, tris-(benzyltriazolylmethyl)amine, that can accelerate the cycloaddition reaction. 10 At the same time, this ligand was found to significantly deter the redox chemistry of Cu(I) with oxygen, which is essential for preventing damage to the oligonucleotides. Encouraged by the highly desirable features of the Cu(I)TBTA-catalyzed azide-alkyne cycloaddition, we studied its applicability to the attachment of oligonucleotide probes onto well-defined SAMs.Oligode...

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“…The later gave efficiently 1,4 disubstituted 1,2,3-triazoles under mild conditions (276,277 give the 1,4-disubstituted triazole-linked C-disaccharide (153 , whereas the corresponding reaction in dichloromethane gave only 43% conversion and 12% ee even with longer reaction time (60 min; Table 5). …”

Section: Click Chemistrymentioning

confidence: 99%

Selective chemical reactions in supercritical carbon dioxide, water, and ionic liquids

Skouta

2009

Green Chemistry Letters and Reviews

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Untitled

Cited by 2,494 publications

References 5 publications

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Chemoselective Covalent Coupling of Oligonucleotide Probes to Self-Assembled Monolayers

Selective chemical reactions in supercritical carbon dioxide, water, and ionic liquids

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