Relevant bibliographies by topics / Azide-alkyne cycloaddition

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Azide-alkyne cycloaddition'

Author: Grafiati
Published: 4 June 2021
Last updated: 9 February 2022

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Journal articles on the topic "Azide-alkyne cycloaddition"

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Cormier, Morgan, Eric Fouquet, and Philippe Hermange. "Expedient synthesis of a symmetric cycloheptyne-Co2(CO)6 complex for orthogonal Huisgen cycloadditions." Organic Chemistry Frontiers 6, no. 8 (2019): 1114–17. http://dx.doi.org/10.1039/c9qo00086k.

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A cycloheptyne dicobalt-carbonyl complex with a terminal alkyne was synthesized by a short procedure, and was able to react selectively in Strain Promoted Alkyne Azide Cycloaddition (SPAAC) or Copper Catalysed Alkyne Azide Cycloaddition (CuAAC) depending on the conditions.
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Chen, Ping-Fan, Kung-Kai Kuo, Jaya Kishore Vandavasi, Siva Senthil Kumar Boominathan, Chung-Yu Chen, and Jeh-Jeng Wang. "Metal-free cycloaddition to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-diones." Organic & Biomolecular Chemistry 13, no. 35 (2015): 9261–66. http://dx.doi.org/10.1039/c5ob01322d.

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Ohata, Jun, Farrukh Vohidov, and Zachary T. Ball. "Convenient analysis of protein modification by chemical blotting with fluorogenic “click” reagents." Molecular BioSystems 11, no. 11 (2015): 2846–49. http://dx.doi.org/10.1039/c5mb00510h.

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Kore, Nitin, and Pavel Pazdera. "New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine." Current Organic Synthesis 15, no. 4 (June 12, 2018): 552–65. http://dx.doi.org/10.2174/1570179415666180110152642.

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Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting α-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable, and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.
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Fürniss, Daniel, Timo Mack, Frank Hahn, Sidonie B. L. Vollrath, Katarzyna Koroniak, Ute Schepers, and Stefan Bräse. "Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry." Beilstein Journal of Organic Chemistry 9 (January 10, 2013): 56–63. http://dx.doi.org/10.3762/bjoc.9.7.

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Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described.
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Meldal, Morten, and Christian Wenzel Tornøe. "Cu-Catalyzed Azide−Alkyne Cycloaddition." Chemical Reviews 108, no. 8 (August 2008): 2952–3015. http://dx.doi.org/10.1021/cr0783479.

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Hema, Kuntrapakam, and Kana M. Sureshan. "Topochemical Azide–Alkyne Cycloaddition Reaction." Accounts of Chemical Research 52, no. 11 (October 10, 2019): 3149–63. http://dx.doi.org/10.1021/acs.accounts.9b00398.

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Stone, M. Rhia L., Muriel Masi, Wanida Phetsang, Jean-Marie Pagès, Matthew A. Cooper, and Mark A. T. Blaskovich. "Fluoroquinolone-derived fluorescent probes for studies of bacterial penetration and efflux." MedChemComm 10, no. 6 (2019): 901–6. http://dx.doi.org/10.1039/c9md00124g.

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Fluorescent probes derived from the fluoroquinolone antibiotic ciprofloxacin were synthesised using a Cu(i)-catalysed azide–alkyne cycloaddition (CuAAC) to link a ciprofloxacin azide derivative with alkyne-substituted green and blue fluorophores.
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Nierengarten, Jean-François. "Copper-catalyzed alkyne-azide cycloaddition for the functionalization of fullerene building blocks." Pure and Applied Chemistry 84, no. 4 (December 14, 2011): 1027–37. http://dx.doi.org/10.1351/pac-con-11-08-21.

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In this paper, we report our ongoing progress in the preparation of fullerene-azide or fullerene-alkyne building blocks, allowing their further chemical transformation under the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction conditions.
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Wendler, Felix, Tobias Rudolph, Helmar Görls, Nils Jasinski, Vanessa Trouillet, Christopher Barner-Kowollik, and Felix H. Schacher. "Maleimide-functionalized poly(2-ethyl-2-oxazoline): synthesis and reactivity." Polymer Chemistry 7, no. 13 (2016): 2419–26. http://dx.doi.org/10.1039/c6py00033a.

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Poly(2-ethyl-2-oxazoline)s end-functionalized with a maleimide moiety were prepared from azide-terminated PEtOxx-N3viacopper-catalyzed azide–alkyne cycloaddition (CuAAC) with an alkyne-bearing maleimide (MI).
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Dissertations / Theses on the topic "Azide-alkyne cycloaddition"

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Beveridge, Jennifer Marie. "Copper(I)-catalyzed azide-alkyne cycloaddition with membrane bound lipid substrates." Thesis, Georgia Institute of Technology, 2015. http://hdl.handle.net/1853/53594.

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The bioorthogonal copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction exhibits complex but well-defined kinetics in aqueous and organic solution for soluble azides, alkynes, and ligand-bound copper(I). The kinetic profile in two dimensions, however, for CuAAC systems within a lipid bilayer membrane, has yet to be defined. The effect of triazole formation with lipid membrane-bound components on membrane properties such as fluidity and permeability is also of interest. Azide- and alkyne-functionalized lysolipids were synthesized and incorporated into non-fluid vesicles, which were then subject to CuAAC. The rate order for membrane-bound lipid substrates in non-fluid vesicles was observed to be comperable to that of the reaction in solution. Reactions between vesicles showed evidence of lipid transfer between non-fluid membranes, which has not been previously reported. For intervesicular and intravesicular reactions in non-fluid membranes, the observed reactivity was found to be opposite that of previously published reactions between nucleophiles and electrophiles in fluid lipid systems. Applications of this work include the potential for novel symmetric membrane leaflet labeling, bioorthogonal manipulation of cell and tissue function, and the creation of membranes with precisely controlled properties that may not be available in naturally-occurring membranes.
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Gramlich, Philipp Mathias Edwin. "Selective DNA modification using the Cu(I)-catalyzed alkyne-azide cycloaddition." Göttingen Cuvillier, 2008. http://d-nb.info/990811395/04.

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Brittain, William David George. "Asymmetric synthesis 1,2,3-triazoles utilising the copper-catalysed azide-alkyne cycloaddition." Thesis, University of Birmingham, 2018. http://etheses.bham.ac.uk//id/eprint/8143/.

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The copper-catalysed azide-alkyne cycloaddition (CuAAC) is a highly efficient reaction and is the cornerstone of “click” chemistry. However, unlike many common metal-mediated transformations asymmetric CuAAC variants are relatively sparse. This thesis details asymmetric “click” reactions with Chapter 1 introducing the CuAAC and the asymmetric variants already present in the literature. Chapter 2 outlines research demonstrating the first example of kinetic resolution of an alkyne via a CuAAC reaction. Selectivity factors of up to 22.1 ± 0.5 were obtained and triazoles and alkynes were obtained in ≤ 80% enantiomeric excess (ee). This chapter also contains a study on the simultaneous kinetic resolution of azides and alkynes; azides were obtained in >30% \(e\)\(e\), alkynes in >40% \(e\)\(e\) and a triazolic diastereomeric product was obtained in up to 90% \(e\)\(e\). In Chapter 3 the Bull-James three-component boronic acid assembly is successfully employed for the kinetic resolution of primary amine alkynes with selectivity factors of up to 4.1 obtained. The principle behind the assembly is also elaborated upon in this chapter leading to its use in both dynamic combinatorial chemistry and as a pedagogical tool. Chapter 4 details work on atropisomerism in triazolic systems. A series of novel triazoles, iodotriazoles and triazolium salts were successfully synthesised and their atropisomeric stability probed. Chapter 5 presents feasibility studies towards the asymmetric synthesis of 5,5’-bis(triazoles) and ruthenium olefin metathesis catalysts in the formation of 1,5-triazoles.
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Vartanian, Maida. "Cu(I) catalyzed alkyne-azide cycloaddition as a synthetic tool for the preparation of complex C60 derivatives." Thesis, Strasbourg, 2012. http://www.theses.fr/2012STRAF016.

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La présente thèse décrit la synthèse de briques de base de fullerènes pour la préparation de dispositifs moléculaires photoactifs combinant C60 et porphyrines. La cycloaddition alcyne-azoture catalysée au cuivre (I) a été utilisée comme outil de synthèse pour la préparation des dérivés C60 complexes.L’utilité synthétique de synthons C60 a été montrée avec la préparation d’édifices moléculaires complexes présentant des propriétés spécifiques pour diverses applications. Ainsi, un système photoactif flexible combinant C60 et porphyrine a été synthétisé. Cependant la flexibilité de l’espaceur liant les sous-unités de ce composé conduit à des variations de structurales importantes et complique ainsi l’analyse des études photophysiques.Dans ce contexte, nous nous sommes proposé dans une première partie de la présente thèse de parfaitement contrôler l’orientation et la distance des différentes sous-unités au sein de systèmes C60-donneurs. Afin de répondre à ce besoin, nous avons construit une brique de base de C60 rigide ayant un groupe azoture aromatique. Ainsi, la réaction « click » avec un phénylacétylène conjugué au groupement donneur conduit à un espaceur rigide entre les deux sous-unités.La deuxième partie de ce travail a été consacrée à la synthèse d’hexa-adduits du C60 portant différents groupements fonctionnels. Une méthode de synthèse permettant de préparer des hexa-adduits du C60 fonctionnalisés a été mise au point au laboratoire.Cette stratégie a été modifiée et des composés de C60 comportant dix fonctions azotures et une fonction alcyne protégée ont été synthétisés; dans ce cas il est possible d’introduire dans un premier temps par une réaction click dix groupes fonctionnels. Et dans un second temps; après déprotection de la fonction alcyne, une seconde réaction de click permet alors de greffer un fonctionnel différent
The present PhD thesis manuscript is focused on the use of fullerene building blocks for the preparation of photoactive molecular devices combining C60 and porphyrins. Cu(I) Catalyzed alkyne-azide cycloaddition was used as a synthetic tool for the preparation of complex C60 derivatives. Specifically, in the first part (Chapter II-B), a flexible fullerene-porphyrin triad has been developed and the photophysical studies were performed. The flexible linker between the fullerene core and the azide groups prevented any conformational control on the relative orientation and distance between the two photoactive subunits connected together. This prompted the development of an analogous building block in which the azide unit is directly connected to the bridging phenyl ring (Chapter II-C). In this way, the click reaction with porphyrin-alkyne derivatives give access to hybrid systems with a controlled relative orientation of the two moieties. This is of fundamental importance for a better understanding of the structural parameters affecting the electron and/or energy transfer kinetic in such dyads.In the second part (Chapter III), a fullerene hexaadduct scaffold is used to build up sophisticated multiporphyrin systems for various applications. The preparation of these multi-chromophoric ensembles relies on the click-click approach developed in our group
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Decan, Matthew. "The Copper(I)-catalyzed Azide–Alkyne Cycloaddition: A Modular Approach to Synthesis and Single-Molecule Spectroscopy Investigation into Heterogeneous Catalysis." Thesis, Université d'Ottawa / University of Ottawa, 2014. http://hdl.handle.net/10393/31882.

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Click chemistry is a molecular synthesis strategy based on reliable, highly selective reactions with thermodynamic driving forces typically in excess of 20 kcal mol-1. The 1,3-dipolar cycloaddition of azides and alkynes developed by Rolf Huisgen saw dramatic rate acceleration using Cu(I) as a catalyst in 2002 reports by Barry Sharpless and Morten Meldal enabling its click chemistry eligibility. Since these seminal reports, the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) has become the quintessential click reaction finding diverse utility. The popularity of the CuAAC has naturally led to interest in new catalyst systems with improved efficiency, robustness, and reusability with particular focus on nanomaterial catalysts, a common trend across the field of catalysis. The high surface area of nanomaterials lends to their efficacy as colloidal and heterogeneous nanocatalysts, but the latter boasts the added benefit of easy separation and recyclability. With any heterogeneous catalyst, a common question arises as to whether the active catalyst species is truly heterogeneous or rather homogeneous through metal ion leaching. Differentiating these processes is critical, as the latter would result in reduced efficiency, higher cost, and inevitable environmental and heath side effects. This thesis explores the CuAAC from an interdisciplary approach. First as a synthetic tool, applying CuAAC-formed triazoles as functional, modular building blocks in the synthesis of optical cation sensors by combining azide and alkyne modified components to create a series of sensors selective for different metal cations. Next, single-molecule spectroscopy techniques are employed to observe the CuNP-catalyzed CuAAC in real time. Combining bench-top techniques with single-molecule microscopy to monitor single-catalytically generated products proves to be an effective method to establish catalysis occurs directly at the surface of copper nanoparticles, ruling out catalysis by ions leached into solution. This methodology is extended to mapping the catalytic activity of a commercial heterogeneous catalyst by applying super-localization analysis of single-catalytic events. The approach detailed herein is a general one that can be applied to any catalytic system through the development of appropriate probes. This thesis demonstrates single-molecule microscopy as an accessible, effective, and unparalleled tool for exploring the catalytic activity of nanomaterials by monitoring single-catalytic events as they occur.
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Happ, Bobby [Verfasser], Ulrich Sigmar [Akademischer Betreuer] Schubert, and Benjamin [Akademischer Betreuer] Dietzek. "Copper(I)-catalyzed azide-alkyne cycloaddition as synthetic tool for triazole-based ligands / Bobby Happ. Gutachter: Ulrich S. Schubert ; Benjamin Dietzek." Jena : Thüringer Universitäts- und Landesbibliothek Jena, 2012. http://d-nb.info/1029294267/34.

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Sharma, Krishna. "Strain-promoted stapled peptides for inhibiting protein-protein interactions." Thesis, University of Cambridge, 2019. https://www.repository.cam.ac.uk/handle/1810/288602.

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Protein-protein interactions (PPIs) are responsible for the regulation of a variety of important functions within living organisms. Compounds which can selectively modulate aberrant PPIs are novel therapeutic candidates for treating human diseases. Whilst PPIs have traditionally been considered as "undruggable", research in this area has led to the emergence of several effective methodologies for targeting PPIs. One such methodology is peptide stapling, which involves constraining a short peptide into its native alpha-helical form by forming a covalent link between two of its amino acid side-chains. The Sondheimer dialkyne reagent has previously been used in strain-promoted double-click cycloadditions with diazidopeptides to generate stapled peptides that are capable of inhibiting PPIs. However, the Sondheimer dialkyne suffers from poor water-solubility; it decomposes rapidly in aqueous solutions which limits its application in biological systems. This dissertation describes the design and synthesis of new substituted variants of the Sondheimer dialkyne with increased solubility and stability, that are suitable for application in strain promoted double click peptide stapling. In total, ten different derivatives were generated; of these, a meta-trimethylammonium substituted variant was found to have particularly high water-solubility and aqueous stability, as well as high azide reactivity. The substituted Sondheimer dialkynes were applied to the strain promoted double click stapling of p53-based diazido peptides in an effort to generate stapled peptide-based inhibitors of the oncogenic p53 MDM2 PPI, a validated target for anticancer therapeutics. Three stapled peptides were found to have inhibitory activity, thus demonstrating the utility of the novel dialkynes in the preparation of PPI inhibitors. The functionalised stapled peptide formed from a meta-fluoro substituted Sondheimer dialkyne was found to be the most potent inhibitor. All ortho-substituted Sondheimer dialkynes were found to be unreactive, whereas those with a meta-trimethylammonium substituent were highly reactive when compared to other meta-substituted dialkynes. These patterns in azide reactivity could be explained through X-ray crystallographic studies and density functional theory calculations.
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Wang, Huifeng. "Molecular Mass Dependent Mechanical Properties of Metal-free Click Hydrogels." University of Akron / OhioLINK, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=akron1427901118.

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Okabayashi, Yohei. "Synthesis of azide- and alkyne-terminated alkane thiols and evaluation of their application in Huisgen 1,3-dipolar cycloaddition ("click") reactions on gold surfaces." Thesis, Department of Physics, Chemistry and Biology, 2009. http://urn.kb.se/resolve?urn=urn:nbn:se:liu:diva-20559.

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Immobilization of different bio- and organic molecules on solid supports is fundamental within many areas of science. Sometimes, it is desirable to obtain a directed orientation of the molecule in the immobilized state. In this thesis, the copper (I) catalyzed Huisgen 1,3-dipolar cycloaddition, referred to as a “click chemistry” reaction, was explored as a means to perform directed immobilization of small molecule ligands on gold surfaces. The aim was to synthesize alkyne- and azide-terminated alkanethiols that would form well-organized self assembled monolayers (SAMs) on gold from the commercially available substances orthoethylene glycol and bromo alkanoic acid. N-(23-azido-3,6,9,12,15,18,21-heptaoxatricosyl)-n-mercaptododekanamide/hexadecaneamide (n = 12, 16) were successfully synthesized and allowed to form SAMs of different compositions to study how the differences in density of the functional groups on the surface would influence the structure of the monolayer and the click chemistry reaction. The surfaces were characterized by different optical methods: ellipsometry, contact angle goniometry and infrared reflection-absorption spectroscopy (IRAS). The click reaction was found to proceed at very high yields on all investigated surfaces. Finally, the biomolecular interaction between a ligand immobilized by click chemistry on the gold surfaces and a model protein (bovine carbonic anhydrase) was demonstrated by surface plasmon resonance using a Biacore system.

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Zhang, Li. "Ruthenium-catalyzed azide-alkyne cycloaddition, and cyclometallation of 2-vinylpyridine with MCl[subscript 2](PPh[subscript 3])[subscript 3] and MHCl(PPh[subscript 3])[subscript 3] (M=Ru, Os) /." View abstract or full-text, 2008. http://library.ust.hk/cgi/db/thesis.pl?CHEM%202008%20ZHANG.

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Book chapters on the topic "Azide-alkyne cycloaddition"

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Finn, M. G., and Valery V. Fokin. "Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC)." In Catalysis without Precious Metals, 235–60. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2010. http://dx.doi.org/10.1002/9783527631582.ch10.

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Cal, Pedro M. S. D., Gonçalo J. L. Bernardes, and Omar Boutureira. "Fluoroglycoproteins by Copper-Free Strain-Promoted Azide–Alkyne Cycloaddition." In Springer Protocols Handbooks, 53–67. New York, NY: Springer US, 2020. http://dx.doi.org/10.1007/978-1-0716-0720-6_5.

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García-Álvarez, Joaquín, and José Gimeno. "“Click” Copper Catalyzed Azide-Alkyne Cycloaddition (CUAAC) in Aqueous Medium." In Advances in Organometallic Chemistry and Catalysis, 199–206. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118742952.ch15.

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Buckley, Benjamin R., and Harry Heaney. "Mechanistic Investigations of Copper(I)-Catalysed Alkyne–Azide Cycloaddition Reactions." In Topics in Heterocyclic Chemistry, 1–29. Berlin, Heidelberg: Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/7081_2011_71.

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Presolski, Stanislav. "Modification of Protein Scaffolds via Copper-Catalyzed Azide–Alkyne Cycloaddition." In Methods in Molecular Biology, 187–93. New York, NY: Springer New York, 2018. http://dx.doi.org/10.1007/978-1-4939-7893-9_14.

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Díaz Arado, Oscar, Harry Mönig, and Harald Fuchs. "On-Surface Synthesis by Azide–Alkyne Cycloaddition Reactions on Metal Surfaces." In Advances in Atom and Single Molecule Machines, 101–14. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-26600-8_5.

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Hoogstede, Freek A. B. M., and Floris P. J. T. Rutjes. "Applications of the Cu-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) in Peptides." In Click Reactions in Organic Synthesis, 141–59. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2016. http://dx.doi.org/10.1002/9783527694174.ch5.

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Straub, Bernd F., Michael Bessel, and Regina Berg. "Dicopper Catalysts for the Azide Alkyne Cycloaddition: A Mechanistic DFT Study." In Modeling of Molecular Properties, 207–14. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527636402.ch13.

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Hussein, Waleed M., Istvan Toth, and Mariusz Skwarczynski. "Peptide-Polymer Conjugation Via Copper-Catalyzed Alkyne-Azide 1,3-Dipolar Cycloaddition." In Methods in Molecular Biology, 1–7. New York, NY: Springer US, 2021. http://dx.doi.org/10.1007/978-1-0716-1617-8_1.

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Hussein, Waleed M., and Istvan Toth. "Peptide-Pegylated Lipid Conjugation Via Copper-Catalyzed Alkyne-Azide 1,3-Dipolar Cycloaddition." In Methods in Molecular Biology, 57–64. New York, NY: Springer US, 2021. http://dx.doi.org/10.1007/978-1-0716-1617-8_6.

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Conference papers on the topic "Azide-alkyne cycloaddition"

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Galindo, Christophe, Françoise Soyer, and Pierre Le Barny. "Copper(I)-catalyzed azide-alkyne cycloaddition for the synthesis of nonlinear electro-optic side-chain copolymers." In Security + Defence, edited by Colin Lewis, Douglas Burgess, Roberto Zamboni, François Kajzar, and Emily M. Heckman. SPIE, 2010. http://dx.doi.org/10.1117/12.864232.

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