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A General Strategy for Visible-Light Decaging Based on the Quinone Trimethyl Lock

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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jacs.7b01548DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jacs.7b01548PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.7b01548PublisherSupporting Information
ORCID:
AuthorORCID
Dougherty, Dennis A.0000-0003-1464-2461
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.
Funders:
Funding AgencyGrant Number
W. M. Keck FoundationUNSPECIFIED
Issue or Number:13
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:03 Oct 2019 16:50

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