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Issue 11, 2013
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The Ugi four-component reaction enables expedient synthesis and comparison of photoaffinity probes

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Abstract

Photoaffinity probes are increasingly being used for the study of biological interactions; however, the lack of structure–activity relationship studies has hindered their rational application. We describe the use of the Ugi four-component reaction (U-4CR) for the expedient and versatile assembly of photoaffinity scaffolds that can be linked to small molecule probes. The rates, yields and sites of crosslinking of five commonly used photoreactive groups comprising diazirines, aryl azides and a benzophenone, were compared using a human 2-oxoglutarate oxygenase as a model protein. The results reveal significant differences in the behavior of the probes and suggest that empirically guided optimization of probes for specific tasks is desirable. In the absence of such optimization it may be advisable to use a set of crosslinking probes/conditions; the U-4CR provides a convenient method for obtaining such a set.

Graphical abstract: The Ugi four-component reaction enables expedient synthesis and comparison of photoaffinity probes

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Supplementary files

Article information


Submitted
19 Jun 2013
Accepted
17 Jul 2013
First published
18 Jul 2013

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2013,4, 4115-4120
Article type
Edge Article

The Ugi four-component reaction enables expedient synthesis and comparison of photoaffinity probes

J. T. Bush, L. J. Walport, J. F. McGouran, I. K. H. Leung, G. Berridge, S. S. van Berkel, A. Basak, B. M. Kessler and C. J. Schofield, Chem. Sci., 2013, 4, 4115
DOI: 10.1039/C3SC51708J

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
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    [Original citation] - Published by the PCCP Owner Societies.
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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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    [Original citation] - Published by The Royal Society of Chemistry.

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