Academic literature on the topic 'Strain-promoted alkyne-azide cycloaddition'

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Journal articles on the topic "Strain-promoted alkyne-azide 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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Lauer, Milena Helmer, Charlotte Vranken, Jochem Deen, et al. "Methyltransferase-directed covalent coupling of fluorophores to DNA." Chemical Science 8, no. 5 (2017): 3804–11. http://dx.doi.org/10.1039/c6sc04229e.

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Cai, Xuekang, Dan Wang, Yasi Gao, Long Yi, Xing Yang, and Zhen Xi. "Tetra-fluorinated aromatic azide for highly efficient bioconjugation in living cells." RSC Advances 9, no. 1 (2019): 23–26. http://dx.doi.org/10.1039/c8ra09303b.

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Liu, Xifeng, Ping Gong, Pengfei Song, et al. "Fast functionalization of ultrasound microbubbles using strain promoted click chemistry." Biomaterials Science 6, no. 3 (2018): 623–32. http://dx.doi.org/10.1039/c8bm00004b.

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Amgarten, Beatrice, Rakesh Rajan, Nuria Martínez-Sáez, et al. "Collagen labelling with an azide-proline chemical reporter in live cells." Chemical Communications 51, no. 25 (2015): 5250–52. http://dx.doi.org/10.1039/c4cc07974d.

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Biosynthetic incorporation of an azide-proline chemical reporter into collagen allows selective imaging in live foetal ovine osteoblasts using a strain-promoted [3+2] azide–alkyne cycloaddition reaction.
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Moon, Jeongbin, In-Seong Jo, Jeong Hoon Yoon, et al. "DNA functionalization of colloidal particles via physisorption of azide-functionalized diblock copolymers." Soft Matter 15, no. 35 (2019): 6930–33. http://dx.doi.org/10.1039/c9sm01243e.

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DNA-coated colloids are prepared simply by physical adsorption of azide-functionalized amphiphilic diblock copolymers onto hydrophobic inorganic particles, followed by strain-promoted azide–alkyne cycloaddition (SPAAC) reaction.
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Engel, Annikka, Eike Dornsiepen, and Stefanie Dehnen. "Click reactions and intramolecular condensation reactions on azido-adamantyl-functionalized tin sulfide clusters." Inorganic Chemistry Frontiers 6, no. 8 (2019): 1973–76. http://dx.doi.org/10.1039/c9qi00424f.

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Tian, He, Thomas P. Sakmar, and Thomas Huber. "A simple method for enhancing the bioorthogonality of cyclooctyne reagent." Chemical Communications 52, no. 31 (2016): 5451–54. http://dx.doi.org/10.1039/c6cc01321j.

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Liu, Xueping, Ying Wu, Minghui Zhang, and Ke Zhang. "Efficient polymer dimerization method based on self-accelerating click reaction." RSC Advances 10, no. 12 (2020): 6794–800. http://dx.doi.org/10.1039/c9ra09919k.

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A convenient and efficient method was developed to prepare topological polymers with a symmetric molecular structure by dimerizing azide terminated polymers based on the self-accelerating double strain-promoted azide–alkyne cycloaddition reaction.
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Weterings, Jimmy, Cristianne J. F. Rijcken, Harald Veldhuis, et al. "TMTHSI, a superior 7-membered ring alkyne containing reagent for strain-promoted azide–alkyne cycloaddition reactions." Chemical Science 11, no. 33 (2020): 9011–16. http://dx.doi.org/10.1039/d0sc03477k.

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Dissertations / Theses on the topic "Strain-promoted alkyne-azide cycloaddition"

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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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Silantyeva, Elena A. "Functionalized Nanofiber Substrates for Nerve Regeneration." University of Akron / OhioLINK, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=akron1555582661302756.

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Book chapters on the topic "Strain-promoted alkyne-azide cycloaddition"

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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. Springer US, 2020. http://dx.doi.org/10.1007/978-1-0716-0720-6_5.

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Kern, Michael, and Sébastien Ferreira-Cerca. "Differential Translation Activity Analysis Using Bioorthogonal Noncanonical Amino Acid Tagging (BONCAT) in Archaea." In Ribosome Biogenesis. Springer US, 2022. http://dx.doi.org/10.1007/978-1-0716-2501-9_14.

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AbstractThe study of protein production and degradation in a quantitative and time-dependent manner is a major challenge to better understand cellular physiological response. Among available technologies bioorthogonal noncanonical amino acid tagging (BONCAT) is an efficient approach allowing for time-dependent labeling of proteins through the incorporation of chemically reactive noncanonical amino acids like l-azidohomoalanine (L-AHA). The azide-containing amino-acid derivative enables a highly efficient and specific reaction termed click chemistry, whereby the azide group of the L-AHA reacts with a reactive alkyne derivate, like dibenzocyclooctyne (DBCO) derivatives, using strain-promoted alkyne–azide cycloaddition (SPAAC). Moreover, available DBCO containing reagents are versatile and can be coupled to fluorophore (e.g., Cy7) or affinity tag (e.g., biotin) derivatives, for easy visualization and affinity purification, respectively.Here, we describe a step-by-step BONCAT protocol optimized for the model archaeon Haloferax volcanii, but which is also suitable to harness other biological systems. Finally, we also describe examples of downstream visualization, affinity purification of L-AHA-labeled proteins and differential expression analysis.In conclusion, the following BONCAT protocol expands the available toolkit to explore proteostasis using time-resolved semiquantitative proteomic analysis in archaea.
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Harris, T., and I. V. Alabugin. "4.1 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC): Background, Substrate Preparation, and Reactivity." In Click Chemistry. Georg Thieme Verlag KG, 2022. http://dx.doi.org/10.1055/sos-sd-235-00143.

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Jonker Anika M., Löwik Dennis W.P.M., and van Hest Jan C.M. "Bio-inspired cross-linking methods for hydrogel formation." In Self Healing Materials. IOS Press, 2015. https://doi.org/10.3233/978-1-61499-514-2-27.

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Hydrogels are water swollen polymeric networks, capable of absorbing large amounts of water or biological fluids. The network is formed by cross-links between the polymeric constituents. These cross-links can either be physical or chemical. Chemical cross-linking methods have the advantage that the cross-linking density can easily be varied and with this also the mechanical properties of the final hydrogel. Physically cross-linked hydrogels are on the other hand adaptive and self-healing by nature. A combined chemically and physically cross-linked network could have highly interesting features from a self-healing materials point of view. In recent years, a number of chemical reactions have been utilized for hydrogel cross-linking. Since hydrogels hold great promise in a variety of biomedical applications, there is a need for novel cross-linking methods, especially those that are biocompatible. In this article, we describe the biocompatible cross-linking reaction SPAAC (strain-promoted azide-alkyne cycloaddition). In the SPAAC reaction, the highly selective reaction between a ring strained alkyne (BCN) and an azide simply occurs in water without any other additives. Poly(ethylene)glycol (PEG) hydrogels were successfully formed using SPAAC as the cross-linking method. We especially focussed on preparing soft hydrogels, mimicking the stiffness of soft body tissues. Confocal microscopy studies performed on the hydrogels revealed that gels containing the cell-adhesion peptide RGDS are a good substrate for cellular adherence. One of the disadvantages we encountered when using SPAAC was that it is hampered by slow reaction kinetics. Furthermore, an activatable cross-linking method is desired, especially in the field of injectable hydrogels. We therefore developed a novel cross-linking method which is both fast and activatable. This fast reaction between a catechol (DHPA) and BCN was called SPOCQ (strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition). The SPOCQ reaction only occurs upon oxidation of the DHPA (catechol) which can be performed both chemically and enzymatically. Both oxidation methods resulted in fast hydrogel formation. We showed that the SPOCQ and SPAAC reaction can be used in one pot, SPOCQ for the fast hydrogel formation and subsequently the SPAAC reaction for functionalization of these hydrogels. We also give an outlook on combining these chemical cross-linking methods with physical cross-linking by incorporation of the calcium-binding motif alendronic acid.
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Arkenberg, Matthew R., Min Hee Kim, and Chien-Chi Lin. "Click Hydrogels for Biomedical Applications." In Multicomponent Hydrogels. The Royal Society of Chemistry, 2023. http://dx.doi.org/10.1039/bk9781837670055-00155.

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Hydrogels crosslinked by homopolymerization of single component acrylate/methacrylate terminated polymers (e.g., poly(ethylene glycol) diacrylate, or PEGDA) were once the dominant biomaterials in biomedical applications, including the encapsulation of therapeutic agents and biological molecules. However, accumulating evidence has revealed many disadvantages of homopolymerized hydrogels, including heterogeneity of the crosslinking that adversely impacted the bioactivity of the encapsulated molecules. As such, recent years have witnessed the expansive use of modular click chemistry for the crosslinking of multicomponent hydrogels, typically consisting of two or more functionally distinct macromolecular building blocks. This chapter provides an overview of the crosslinking and applications of multicomponent hydrogels, focusing on those crosslinked by strain-promoted alkyne–azide cycloaddition (SPAAC), Michael-type addition, Diels–Alder (DA) reactions, inverse electron-demand Diels–Alder (iEDDA), thiol–ene polymerizations, and imine/hydrazone/oxime click reactions. This chapter also summarizes information regarding the characteristics, advantages, and limitations of commonly used synthetic (e.g., PEG, poly(acrylate), poly(vinyl alcohol), etc.) and naturally-derived macromers (e.g., gelatin, hyaluronic acid, etc.) for forming multicomponent hydrogels. Finally, an overview is given on the applications of multicomponent hydrogels in drug delivery, biofabrication, and 3D/4D cell culture.
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Vrabel, M. "2 From Biological Chemistry to Bioorthogonal Reactions." In Abiotic Reactions in Live Environments. Georg Thieme Verlag KG, 2025. https://doi.org/10.1055/sos-sd-242-00069.

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AbstractThis contribution aims to trace the origins of bioorthogonal chemistry, from its roots in early alchemy and the Scientific Revolution, to its development as a response to the quest to understand the fundamental principles of life. The development and application of chemical tools to study and manipulate biological processes and biomolecules laid the foundation for modern chemical biology. With the advent of the first chemical reactions that proceed selectively and efficiently without interfering with biological systems, scientists gained a unique set of tools to achieve an unprecedented level of understanding of biological processes at the molecular level. New techniques such as strain-promoted azide–alkyne cycloaddition (SPAAC), tetrazine ligation, and artificial metalloenzymes have further advanced the field. These modern tools of chemistry have significantly extended the potential of bioorthogonal chemistry and hold the promise of revolutionizing healthcare through improved drug delivery and advanced diagnostic tools. By placing these achievements in the context of the history of science, it is clear that this field has a bright future. As our understanding of bioorthogonal reactions deepens and technology evolves, we can anticipate their incorporation into a wide range of practices, potentially ushering in a new era of advanced personalized treatments.
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