Abstract
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
Current Organic Chemistry
Title:Application of Metal Free Click Chemistry in Biological Studies
Volume: 17 Issue: 6
Author(s): Pavels Ostrovskis, Chandra M. R. Volla, Maris Turks and Dean Markovic
Affiliation:
Keywords: Biological applications, Bioorthogonal chemistry, Click chemistry, Cycloadditions, Staudinger-Bertozzi ligation, Thio-click chemistry
Abstract: 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.
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Cite this article as:
Ostrovskis Pavels, M. R. Volla Chandra, Turks Maris and Markovic Dean, Application of Metal Free Click Chemistry in Biological Studies, Current Organic Chemistry 2013; 17 (6) . https://dx.doi.org/10.2174/1385272811317060006
DOI https://dx.doi.org/10.2174/1385272811317060006 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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