Click Chemistry Biomolecular Engineering - Presentation - Yeshitila.pptx

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Click Chemistry Biomolecular Engineering - Presentation - Yeshitila.pptx

  1. 1. Click Chemistry<br />Click Chemistry & Its Role in Biomolecular Engineering<br />By: Yeshitila Asteraye Tsigie (PhD Student)<br />National Taiwan University of Science and Technology<br />
  2. 2. Contents<br />Introduction<br />Click Chemistry<br />Applications of Click Chemistry<br />Conclusions<br />2<br />
  3. 3. Introduction<br />K.B. Sharpless<br />2001<br /> Nobel Prize in Chemistry and introducing the concept “Click Chemistry” ??????????????.<br />3<br />
  4. 4. Introduction (Cont…)<br />Some Important Terms<br />Functional Groups<br /> sites of chemical reactivity in an organic compound <br />Biomolecules<br />Organic building blocks of organisms<br />4<br />
  5. 5. Introduction (Cont…)<br />Nature generates substances by joining small molecular units.<br />5<br />
  6. 6. 6<br />
  7. 7. Is it possible to generate larger molecules from small molecules in the laboratory? <br />7<br />
  8. 8. Click Chemistry<br />describes chemical reactions that generate substances quickly, reliably and in quantitative yield by joining small building blocks under mild conditions. <br />is inspired by the fact that chemical reactions in nature also generate substances by joining small molecular units.<br />8<br />
  9. 9. Click Chemistry (Cont…)<br />a new way of thinking molecular construction. <br /> is based on the use of fast and efficient reactions between building blocks <br /> permits the construction of highly diversified structures through the use of reactive subunits.<br />9<br />
  10. 10. Why Click Chemistry is different from chemistry of native biomolecules????<br /><ul><li>It is very selective
  11. 11. only between azide and alkyne components.
  12. 12. It is does not interfere with most any other organic groups present in DNA and proteins being labeled, such as amino and carboxy groups.
  13. 13. There are no azides and alkynes in native biomolecules.
  14. 14. These groups should be specially introduced into DNA and proteins.
  15. 15. Click Chemistry takes place in water.
  16. 16. Aqueous DMSO, DMF, acetonitrile, alcohols, or pure water and buffers can be used for the reaction.
  17. 17. The reaction is biocompatible and can take place in living cells.
  18. 18. Reaction is quick and quantitative.
  19. 19. The reaction is pH-insensitive.
  20. 20. no need to control pH in reaction mixture.
  21. 21. works well in pH interval of 4-11.
  22. 22. Most click reactions involve the formation of carbon–heteroatom (mostly N, O, and S) bonds.</li></ul>10<br />
  23. 23. WhyAzide and Alkyne Groups?<br />built-in high energy content<br />‘invisible’ in all terrestrial environments<br />but, when properly introduced, they ‘click’ forming an indestructible triazolelink<br />11<br />
  24. 24. Reactions in Click Chemistry<br />Nucleophilic substitutions<br />Electrophilic substitutions<br />Ring opening <br />. Cycloadditions reactions such as the copper (I)-modified Huisgen reaction<br />. Diels-Alder reaction<br />12<br />
  25. 25. Huisgen’s [1,3] Dipolar Cycloaddition<br />13<br />
  26. 26. CuAAC - Cu catalyzed alkyneazidecycloaddition (CuAAC Ligation)<br />The most popular reaction which fulfills “click reaction”<br />14<br />
  27. 27. Mechanism of CuAAC Click Reaction<br />15<br />
  28. 28. Applications of Click Chemistry<br />16<br />
  29. 29. Synthesis of N-Terminally Linked Protein Dimers and Trimers<br />17<br />
  30. 30. Copper-free click chemistry in living animals<br />To label azidosugars<br />www.pnas.org/cgi/doi/10.1073/pnas.0911116107<br />18<br />
  31. 31. To prepare functionalized poly(alkyl cyanoacrylate) nanoparticles<br />19<br />
  32. 32. Preparation of Covalently Stabilized Thermoresponsive Microcapsules layer-by-layer<br />20<br />
  33. 33. Preparation of Sliding Supramolecular Polymer Brushes (SSPBs)<br />21<br />
  34. 34. Assembling Ferromagnetic FePtNano-particles as SAM<br />22<br />
  35. 35. Site-Selective Functionalization of a TubularlyAssembled Hexabenzocoronene<br />23<br />
  36. 36. Bioconjugated Janus Particles preparation<br />24<br />
  37. 37. Dendrimer Synthesis<br />25<br />
  38. 38. Labellingoligonucleotides with carbohydrates<br />26<br />
  39. 39. Functionalization of Gold Nanoparticles and Linking to Lipase<br />27<br />
  40. 40. Conclusions<br />Click Chemistry<br />Newly emerging field of chemistry<br />Aqueous environment<br />Selective and specific<br />Fast<br />Efficient<br />Used for synthesizing biologically important compounds<br />Is based on nature’s principle of producing macromolecules from small building blocks<br />28<br />
  41. 41. 29<br />Thank You For Your Attention!!!<br />

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