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Competing pathways for photoremovable protecting groups: the effects of solvent, oxygen and encapsulation

2020-10Artigo científico Acesso restrito
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dc.contributor.authorField, Thomas
dc.contributor.authorPeterson, Julie
dc.contributor.authorMa, Chicheng
dc.contributor.authorJagadesan, Pradeepkumar
dc.contributor.authorDa Silva, José Paulo
dc.contributor.authorRubina, Marina
dc.contributor.authorRamamurthy, V.
dc.contributor.authorGivens, Richard S.
dc.date.accessioned2021-06-24T11:35:11Z
dc.date.available2021-06-24T11:35:11Z
dc.date.issued2020-10
dc.description.abstractExtending the applications of Photoremovable Protecting Groups (PPGs) to "cage" phenols has generally met with unusually complex PPG byproducts. In this study, we demonstrate that thep-hydroxyphenacyl (pHP) cage for both simple and complex phenolics, including tyrosine, dispenses free phenols. With the simpler unsubstituted phenols, the reaction is governed by their Bronsted Leaving Group ability. On the other hand, the byproducts of the cage vary with these phenols. For the more acidic phenols the cage byproduct follows the Favorskii rearrangement to formp-hydroxyphenylacetic acid whereas for the weaker phenols other reactions such as reduction and hydrolysis begin to emerge. When the photolysis is conducted in octa acid (OA) containers, non-Favorskii, unrearranged fragments of the cage and other byproducts arise.
dc.description.sponsorshipKansas University Endowment Association
dc.description.sponsorshipNational Institutes of HealthUnited States Department of Health & Human ServicesNational Institutes of Health (NIH) - USA
dc.description.sponsorshipNational Science FoundationNational Science Foundation (NSF) [CHE-1807729]
dc.description.sponsorshipFCT - Foundation for Science and TechnologyPortuguese Foundation for Science and Technology [UID/Multi/04326/2019]
dc.description.sponsorshipoperational program COMPETE 2020 [EMBRC.PT ALG-01-0145-FEDER-022121]
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1039/d0pp00067a
dc.identifier.issn1474-905X
dc.identifier.urihttp://hdl.handle.net/10400.1/16366
dc.language.isoeng
dc.peerreviewedyes
dc.publisherSpringer
dc.relationCentre of Marine Sciences
dc.subject.otherBiochemistry & Molecular Biology
dc.titleCompeting pathways for photoremovable protecting groups: the effects of solvent, oxygen and encapsulation
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCentre of Marine Sciences
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMulti%2F04326%2F2019/PT
oaire.citation.endPage1372
oaire.citation.issue10
oaire.citation.startPage1364
oaire.citation.titlePhotochemical & Photobiological Sciences
oaire.citation.volume19
oaire.fundingStream6817 - DCRRNI ID
person.familyNameSilva
person.givenNameJosé Paulo da
person.identifier.ciencia-id3413-C4F4-73F7
person.identifier.orcid0000-0002-6458-7328
person.identifier.ridA-4606-2008
person.identifier.scopus-author-id7201733236
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccess
rcaap.typearticle
relation.isAuthorOfPublicatione2004fa2-a47d-44b0-b11c-fc95fe51cbf9
relation.isAuthorOfPublication.latestForDiscoverye2004fa2-a47d-44b0-b11c-fc95fe51cbf9
relation.isProjectOfPublicationf38dbd9d-3734-4f3c-8d74-dff8dcaa8674
relation.isProjectOfPublication.latestForDiscoveryf38dbd9d-3734-4f3c-8d74-dff8dcaa8674

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