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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Application of Metal Free Click Chemistry in Biological Studies

Author(s): Pavels Ostrovskis, Chandra M. R. Volla, Maris Turks and Dean Markovic

Volume 17, Issue 6, 2013

Page: [610 - 640] Pages: 31

DOI: 10.2174/1385272811317060006


The first reported click reaction, copper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition had limited biocompatibility due to the high toxicity of copper. Since alternative bioorthogonal click reactions have been developed, they have strongly influenced the field of chemical biology. Here are summarized three main metal-free click methodologies based on cycloaddition, Staudinger and thioene reactions. This review contains the basic principles, some mechanistic considerations and a collection of reagents that can be used in each method. Firstly, Diels-Alder and strain promoted inverse electron demand Diels-Alder cycloadditions are outlined together with triazole and isoxazole formation by 1,3-dipolar cycloadditions. Secondly, Staudinger-Bertozzi ligation, a chemoselective reaction of azides and engineered triarylphosphines, is discussed. Finally, thio-click chemistries including thiol-ene, thiol-yne, thio-Michael and fluoro-thioclick reactions are reviewed. Among the most important bioapplications of these click methodologies is the labeling of glycans, proteins, lipids and DNA. Additionally, synthetic methods and surface immobilization of biomolecules and biologically useful polymeric materials are also reviewed.

Keywords: Biological applications, Bioorthogonal chemistry, Click chemistry, Cycloadditions, Staudinger-Bertozzi ligation, Thio-click chemistry

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