File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Time-Resolved Spectroscopic Observation of Diphenylnitrenium Ion Reactions with Guanosine

TitleTime-Resolved Spectroscopic Observation of Diphenylnitrenium Ion Reactions with Guanosine
Authors
Issue Date2020
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
The Journal of Organic Chemistry, 2020, v. 85 n. 14, p. 8792-8797 How to Cite?
AbstractArylnitrenium ions have gained attention for their high reactivity toward guanosine, which in some cases has been linked to carcinogenesis. Although many studies have examined covalent addition reactions between arylnitrenium ions and guanosine, there is still some uncertainty regarding the attack position of nitrenium ions on guanosine and its derivatives. In this paper, we employ nanosecond transient absorption and nanosecond time-resolved resonance Raman spectroscopy to investigate the reaction between the N,N-di(4-bromophenyl) nitrenium ion (2) and guanosine. Our time-resolved spectroscopic results and photochemical product analysis results show that the reaction of guanosine with 2 generates an N7 intermediate that subsequently undergoes rearrangement and deprotonation to produce a C8 adduct. Comparing these results to our previous study between the 2-fluorenylnitrenium ion and guanosine indicates that the structure and properties of arylnitrenium ions are able to influence the reaction pathways and intermediate structures.
Persistent Identifierhttp://hdl.handle.net/10722/300772
ISSN
2020 Impact Factor: 4.354
2020 SCImago Journal Rankings: 1.200
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorDu, L-
dc.contributor.authorYAN, Z-
dc.contributor.authorZhu, Z-
dc.contributor.authorCheng, SC-
dc.contributor.authorZhang, Y-
dc.contributor.authorLi, X-
dc.contributor.authorTang, W-
dc.contributor.authorPhillips, DL-
dc.date.accessioned2021-07-06T03:10:02Z-
dc.date.available2021-07-06T03:10:02Z-
dc.date.issued2020-
dc.identifier.citationThe Journal of Organic Chemistry, 2020, v. 85 n. 14, p. 8792-8797-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10722/300772-
dc.description.abstractArylnitrenium ions have gained attention for their high reactivity toward guanosine, which in some cases has been linked to carcinogenesis. Although many studies have examined covalent addition reactions between arylnitrenium ions and guanosine, there is still some uncertainty regarding the attack position of nitrenium ions on guanosine and its derivatives. In this paper, we employ nanosecond transient absorption and nanosecond time-resolved resonance Raman spectroscopy to investigate the reaction between the N,N-di(4-bromophenyl) nitrenium ion (2) and guanosine. Our time-resolved spectroscopic results and photochemical product analysis results show that the reaction of guanosine with 2 generates an N7 intermediate that subsequently undergoes rearrangement and deprotonation to produce a C8 adduct. Comparing these results to our previous study between the 2-fluorenylnitrenium ion and guanosine indicates that the structure and properties of arylnitrenium ions are able to influence the reaction pathways and intermediate structures.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc-
dc.relation.ispartofThe Journal of Organic Chemistry-
dc.rightsThis 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.titleTime-Resolved Spectroscopic Observation of Diphenylnitrenium Ion Reactions with Guanosine-
dc.typeArticle-
dc.identifier.emailDu, L: ailleen@hku.hk-
dc.identifier.emailLi, X: xuechenl@hku.hk-
dc.identifier.emailPhillips, DL: phillips@hku.hk-
dc.identifier.authorityLi, X=rp00742-
dc.identifier.authorityPhillips, DL=rp00770-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.joc.0c00517-
dc.identifier.pmid32527081-
dc.identifier.scopuseid_2-s2.0-85089283999-
dc.identifier.hkuros323194-
dc.identifier.volume85-
dc.identifier.issue14-
dc.identifier.spage8792-
dc.identifier.epage8797-
dc.identifier.isiWOS:000551550500005-
dc.publisher.placeUnited States-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats