454241 Click and Release: Fluoride Cleavable Linker for Mild Bioorthogonal Separation on Magnetic Nanoparticles

Wednesday, November 16, 2016: 8:30 AM
Golden Gate 6 (Hilton San Francisco Union Square)
Elia Schneider1, Vladimir Zlateski2, Martin Zeltner3, Robert N. Grass4 and Wendelin J. Stark4, (1)ETH Zurich Institute for Chemical and Bioengineering, ETH Zurich, Zurich, (2)ETH Zurich, Institute for Chemical and Bioengineering, (3)ETH Zurich, 8093 Zurich, Switzerland, (4)Institute for Chemical and Bioengineering, ETH-Zürich, Zürich, Switzerland

Bioorthogonal chemistry opened the way for a detailed description and understanding of many biological processes. However, these kind of reactions, such as the Staudinger ligation or the 1,3-dipolar Huisgen cycloaddition of azides and alkynes, are not reversible and cannot be cleaved in a specific and bio-compatible way. This would be beneficial for a large set of applications, for example native protein analysis, protein glycosylation analysis and analysis of protein complexes via mass spectroscopy.

Our idea was to implement a cleavable silane moiety, one of the most used protecting groups for alcohols in organic chemistry. The main advantage of this system is the cleavage via fluoride ions, which has already been used in solid peptide synthesis. Our aim was to combine this mature technique to the modern copper-free ‘‘click’’ chemistry. By combining the mature and biorthogonal silane-chemistry with the state-of-the-art copper-free ‘‘click’’- chemistry, creation of a cleavable ‘‘click and release’’ system is anticipated. Additionally, a suitable way to get in and out of a biological system has to be considered. A promising approach is provided by magnetic nanoparticles, since they can be separated quickly from any solution by using a permanent magnet. Therefore, we engineered a system that combines all of these features using carbon-coated cobalt nanoparticles, ATRP-polymerization for antifouling properties and subsequently the mild linker system.

Schneider, E. M.; Zeltner, M.; Zlateski, V.; Grass, R. N.; Stark, W. J. Chem. Commun. 2016, 52, 938

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