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Publikācija: Application of Metal-Free Click Chemistry in Biological Studies

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Application of Metal-Free Click Chemistry in Biological Studies
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Pāvels Ostrovskis
Chandra M. R. Volla
Māris Turks
Dean Markovic
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, the three main metal-free click methodologies based on cycloaddition, Staudinger and thio-ene reactions are summarized. 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-thio-click 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.
DOI: 10.2174/1385272811317060006
Hyperlink: http://www.eurekaselect.com/108828/article 
Reference Ostrovskis, P., Volla, C., Turks, M., Markovic, D. Application of Metal-Free Click Chemistry in Biological Studies. Current Organic Chemistry, 2013, Vol.17, Iss.6, pp.610-640. e-ISSN 1875-5348. ISSN 1385-2728. Available from: doi:10.2174/1385272811317060006
Additional information Citation count:
ID 15687