Walton, David P. and Dougherty, Dennis A. (2017) A General Strategy for Visible-Light Decaging Based on the Quinone Trimethyl Lock. Journal of the American Chemical Society, 139 (13). pp. 4655-4658. ISSN 0002-7863. doi:10.1021/jacs.7b01548. https://resolver.caltech.edu/CaltechAUTHORS:20170327-085512500
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Abstract
Visible-light triggered quinone trimethyl locks are reported as a general design for long-wavelength photoremovable protecting groups for alcohols and amines. Intramolecular photoreduction unmasks a reactive phenol that undergoes fast lactonization to release alcohols and amines. Model substrates are released in quantitative yield along with well-defined, colorless hydroquinone byproducts. Substituent modifications of the quinone core allow absorption from 400 to 600 nm.
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| Additional Information: | © 2017 American Chemical Society. Received: February 13, 2017; Published: March 21, 2017. We thank Clint Regan and Oliver Shafaat for helpful discussions and Chris Marotta for assistance with the electrophysiology experiments. We thank the Beckman Institute of Caltech Laser Resource Center for use of their fluorimeter. This work was supported by the W. M. Keck Foundation. | ||||||||||||
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| Issue or Number: | 13 | ||||||||||||
| DOI: | 10.1021/jacs.7b01548 | ||||||||||||
| Record Number: | CaltechAUTHORS:20170327-085512500 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170327-085512500 | ||||||||||||
| Official Citation: | A General Strategy for Visible-Light Decaging Based on the Quinone Trimethyl Lock David P. Walton and Dennis A. Dougherty Journal of the American Chemical Society 2017 139 (13), 4655-4658 DOI: 10.1021/jacs.7b01548 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 75403 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||
| Deposited On: | 27 Mar 2017 16:02 | ||||||||||||
| Last Modified: | 15 Nov 2021 16:33 |
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