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Structure, Bonding, and Photoaffinity Labeling Applications of Dialkyldiazirines

Zhang, Tianyi and Ondrus, Alison E. (2021) Structure, Bonding, and Photoaffinity Labeling Applications of Dialkyldiazirines. Synlett, 32 (11). pp. 1053-1059. ISSN 0936-5214. doi:10.1055/a-1437-8202. https://resolver.caltech.edu/CaltechAUTHORS:20210420-094312224

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1055/a-1437-8202DOIArticle
ORCID:
AuthorORCID
Zhang, Tianyi0000-0001-8289-3102
Ondrus, Alison E.0000-0002-6023-3290
Additional Information:© 2021. 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/). Received: 28 February 2021; Accepted after revision: 15 March 2021; Publication Date: 15 March 2021 (online). We thank Dr. Y.-S. Cheng and Prof. R. G. Hadt for invaluable input during the preparation of this manuscript. Support was provided by Caltech start-up funds for A.E.O. and a John Stauffer Charitable Trust SURF Fellowship for T.Z. California Institute of Technology. The authors declare no conflict of interest.
Funders:
Funding AgencyGrant Number
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Subject Keywords:diazirine, carbene, photoreactivity, chemical biology, protein-ligand interactions
Issue or Number:11
DOI:10.1055/a-1437-8202
Record Number:CaltechAUTHORS:20210420-094312224
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210420-094312224
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:108771
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:22 Apr 2021 18:51
Last Modified:08 Jul 2021 17:48

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