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- Publisher Website: 10.1021/acs.joc.8b02252
- Scopus: eid_2-s2.0-85055638707
- PMID: 30303366
- WOS: WOS:000449443200047
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Article: Unraveling the Photodeprotection Mechanism of Anthraquinon-2-ylmethoxycarbonyl-Caged Alcohols Using Time-Resolved Spectroscopy
Title | Unraveling the Photodeprotection Mechanism of Anthraquinon-2-ylmethoxycarbonyl-Caged Alcohols Using Time-Resolved Spectroscopy |
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Authors | |
Issue Date | 2018 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | The Journal of Organic Chemistry, 2018, v. 83 n. 21, p. 13454-13462 How to Cite? |
Abstract | Anthraquinone (AQ) compounds have been used as photolabile protecting groups (PPGs) to protect alcohols, ketones, and carboxylic acids. However, because of the lack of direct spectroscopic information for the transient species and intermediates related with the deprotection reaction(s), the photorelease mechanism(s) of these systems are still largely unknown. In this contribution, we detail a time-resolved spectroscopic investigation using anthraquinone-protected galactose (1) and adenosine (2) to investigate the photodeprotection reaction mechanism(s) of these kinds of AQ-PPGs. It was found that, in THF-H2O solvents, the ketyl radical species generated for 1 and 2 was found to be a reactive intermediate that then formed a dihydroxyanthracene species. The photodeprotection then occurred with the accompaniment of a decarboxylation process. These results provide an improved understanding for how AQ-PPGs work and will help assist in the design and applications of selected anthraquinone derivatives as a PPG platform, especially in aqueous environments more relevant for use in biological systems. Copyright © 2018 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/279293 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Guo, Y | - |
dc.contributor.author | Song, Q | - |
dc.contributor.author | Wang, J | - |
dc.contributor.author | Ma, J | - |
dc.contributor.author | Zhang, X | - |
dc.contributor.author | Phillips, DL | - |
dc.date.accessioned | 2019-10-25T13:52:41Z | - |
dc.date.available | 2019-10-25T13:52:41Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | The Journal of Organic Chemistry, 2018, v. 83 n. 21, p. 13454-13462 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/279293 | - |
dc.description.abstract | Anthraquinone (AQ) compounds have been used as photolabile protecting groups (PPGs) to protect alcohols, ketones, and carboxylic acids. However, because of the lack of direct spectroscopic information for the transient species and intermediates related with the deprotection reaction(s), the photorelease mechanism(s) of these systems are still largely unknown. In this contribution, we detail a time-resolved spectroscopic investigation using anthraquinone-protected galactose (1) and adenosine (2) to investigate the photodeprotection reaction mechanism(s) of these kinds of AQ-PPGs. It was found that, in THF-H2O solvents, the ketyl radical species generated for 1 and 2 was found to be a reactive intermediate that then formed a dihydroxyanthracene species. The photodeprotection then occurred with the accompaniment of a decarboxylation process. These results provide an improved understanding for how AQ-PPGs work and will help assist in the design and applications of selected anthraquinone derivatives as a PPG platform, especially in aqueous environments more relevant for use in biological systems. Copyright © 2018 American Chemical Society. | - |
dc.language | eng | - |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | - |
dc.relation.ispartof | The Journal of Organic Chemistry | - |
dc.rights | This document is the Accepted Manuscript version of a Published Work that appeared in final form in [JournalTitle], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html]. | - |
dc.title | Unraveling the Photodeprotection Mechanism of Anthraquinon-2-ylmethoxycarbonyl-Caged Alcohols Using Time-Resolved Spectroscopy | - |
dc.type | Article | - |
dc.identifier.email | Zhang, X: heeteen@hku.hk | - |
dc.identifier.email | Phillips, DL: phillips@hku.hk | - |
dc.identifier.authority | Phillips, DL=rp00770 | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/acs.joc.8b02252 | - |
dc.identifier.pmid | 30303366 | - |
dc.identifier.scopus | eid_2-s2.0-85055638707 | - |
dc.identifier.hkuros | 308136 | - |
dc.identifier.volume | 83 | - |
dc.identifier.issue | 21 | - |
dc.identifier.spage | 13454 | - |
dc.identifier.epage | 13462 | - |
dc.identifier.isi | WOS:000449443200047 | - |
dc.publisher.place | United States | - |
dc.identifier.issnl | 0022-3263 | - |