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CC BY-NC-ND 4.0 · Synlett 2021; 32(11): 1053-1059
DOI: 10.1055/a-1437-8202
DOI: 10.1055/a-1437-8202
synpacts
Structure, Bonding, and Photoaffinity Labeling Applications of Dialkyldiazirines
Support was provided by Caltech start-up funds for A.E.O. and a John Stauffer Charitable Trust SURF Fellowship for T.Z.
Abstract
Dialkyldiazirine photoaffinity probes are unparalleled tools for the study of small molecule–protein interactions. Here we summarize the basic principles of structure, bonding, and photoreactivity of dialkyldiazirines, current methods for their synthesis, and their practical application in photoaffinity labeling experiments. We demonstrate the unique utility of dialkyldiazirine probes in the context of our recent photoaffinity crosslinking-mass spectrometry analysis to reveal a hidden cholesterol binding site in the Hedgehog morphogen proteins.
1 Introduction
2 Structure, Bonding, and Spectral Properties
3 Photoreactivity
4 Synthesis
5 Application in Photoaffinity Labeling
6 Discovery of a Cholesterol–Hedgehog Protein Interface
7 Conclusions and Outlook
Publication History
Received: 28 February 2021
Accepted after revision: 15 March 2021
Accepted Manuscript online:
15 March 2021
Article published online:
09 April 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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