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2021-07-19Zeitschriftenartikel DOI: 10.18452/24525
Toward conditional control of Smac mimetic activity by RNA‐templated reduction of azidopeptides on PNA or 2′‐OMe‐RNA
dc.contributor.authorAltrichter, Yannic
dc.contributor.authorSchöller, Justus
dc.contributor.authorSeitz, Oliver
dc.date.accessioned2022-04-22T13:16:04Z
dc.date.available2022-04-22T13:16:04Z
dc.date.issued2021-07-19none
dc.date.updated2022-03-21T01:13:08Z
dc.identifier.issn0006-3525
dc.identifier.urihttp://edoc.hu-berlin.de/18452/25196
dc.description.abstractOligonucleotide templated reactions can be used to control the activity of functional molecules based on the presence of a specific trigger sequence. We report an RNA‐controlled reaction system to conditionally restore the N‐terminal amino group and thus binding affinity of azide‐modified Smac mimetic compounds (SMCs) for their target protein X‐linked Inhibitor of Apoptosis Protein (XIAP). Two templated reactions were compared: Staudinger reduction with phosphines and a photocatalytic reaction with Ru(bpy)2(mcbpy). The latter proved faster and more efficient, especially for the activation of a bivalent SMC, which requires two consecutive reduction steps. The templated reaction proceeds with turnover when 2′‐OMe‐RNA probes are used, but is significantly more efficient with PNA, catalyzing a reaction in the presence of low, substoichiometric amounts (1%‐3%, 10 nM) of target RNA.eng
dc.description.sponsorshipEuropean Research Council, Horizon 2020 Programme
dc.language.isoengnone
dc.publisherHumboldt-Universität zu Berlin
dc.rights(CC BY 4.0) Attribution 4.0 Internationalger
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectphotocatalytic reductioneng
dc.subjectSmac mimeticseng
dc.subjectStaudinger reductioneng
dc.subjecttemplated chemistryeng
dc.subject.ddc540 Chemie und zugeordnete Wissenschaftennone
dc.subject.ddc570 Biologienone
dc.titleToward conditional control of Smac mimetic activity by RNA‐templated reduction of azidopeptides on PNA or 2′‐OMe‐RNAnone
dc.typearticle
dc.identifier.urnurn:nbn:de:kobv:11-110-18452/25196-3
dc.identifier.doihttp://dx.doi.org/10.18452/24525
dc.type.versionpublishedVersionnone
local.edoc.pages9none
local.edoc.type-nameZeitschriftenartikel
local.edoc.container-typeperiodical
local.edoc.container-type-nameZeitschrift
dc.description.versionPeer Reviewednone
dc.identifier.eissn1097-0282
dcterms.bibliographicCitation.doi10.1002/bip.23466none
dcterms.bibliographicCitation.journaltitleBiopolymersnone
dcterms.bibliographicCitation.volume112none
dcterms.bibliographicCitation.issue12none
dcterms.bibliographicCitation.articlenumbere23466none
dcterms.bibliographicCitation.originalpublishernameWileynone
dcterms.bibliographicCitation.originalpublisherplaceNew York, NYnone
bua.departmentMathematisch-Naturwissenschaftliche Fakultätnone

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