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Ru-Catalyzed C-H Hydroxylation of Tyrosine-Containing Di- and Tripeptides toward the Assembly of L-DOPA Derivatives

dc.contributor.authorAndrade Sampedro, Paula
dc.contributor.authorMatxain Beraza, Jon Mattin ORCID
dc.contributor.authorCorrea Navarro, Arkaitz ORCID
dc.date.accessioned2022-09-08T08:39:46Z
dc.date.available2022-09-08T08:39:46Z
dc.date.issued2022-06-21
dc.identifier.citationAdvanced Synthesis & Catalysis 364(12) : 2072-2079 (2022)es_ES
dc.identifier.issn1615-4150
dc.identifier.issn1615-4169
dc.identifier.urihttp://hdl.handle.net/10810/57483
dc.description.abstract[EN] The development of catalytic tools for the late-stage modification of amino acids within a peptide framework is a challenging task of capital importance. Herein, we report a Ru-catalyzed C(sp(2))-H hydroxylation of a collection of Tyr-containing di- and tripeptides featuring the use of a carbamate as a removable directing group and PhI(OCOCF3)(2) (PIFA) as oxidant. This air-compatible tagging technique is reliable, scalable and provides access to L-DOPA (L-3,4-dihydroxyphenylalanine) peptidomimetics in a racemization-free fashion. Density Functional Theory calculations support a Ru(II)/Ru(IV) catalytic cycle.es_ES
dc.description.sponsorshipWe are grateful to Ministerio de Ciencia e Innovacion (RTI2018-093721-B-I00, MCI/AEI/FEDER, UE) and Basque Government (IT1033-16 and IT1254-19) for financial support. We thank for technical and human support provided by SGIker of UPV/EHU and European funding (ERDF and ESF). P. A.-S. thanks DIPC for the research contract.es_ES
dc.language.isoenges_ES
dc.publisherWileyes_ES
dc.relationinfo:eu-repo/grantAgreement/MICIU/RTI2018-093721-B-I00es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjecthydroxylationes_ES
dc.subjecttyrosinees_ES
dc.subjectruthenium catalysises_ES
dc.subjectpeptideses_ES
dc.subjectC-H functionalizationes_ES
dc.titleRu-Catalyzed C-H Hydroxylation of Tyrosine-Containing Di- and Tripeptides toward the Assembly of L-DOPA Derivativeses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCHGmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial No Derivs License,which permits use and distributionin any medium,provided the origina lwork is properly cited, the use is non-commercial and no modifications or adaptations are made.es_ES
dc.rights.holderAtribución-NoComercial-SinDerivadas 3.0 España*
dc.relation.publisherversionhttps://onlinelibrary.wiley.com/doi/10.1002/adsc.202200234es_ES
dc.identifier.doi10.1002/adsc.202200234
dc.departamentoesPolímeros y Materiales Avanzados: Física, Química y Tecnologíaes_ES
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuPolimero eta Material Aurreratuak: Fisika, Kimika eta Teknologiaes_ES
dc.departamentoeuKimika organikoa Ies_ES


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© 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCHGmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial No Derivs License,which permits use and distributionin any medium,provided the origina lwork is properly cited, the use is non-commercial and no modifications or adaptations are made.
Except where otherwise noted, this item's license is described as © 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCHGmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial No Derivs License,which permits use and distributionin any medium,provided the origina lwork is properly cited, the use is non-commercial and no modifications or adaptations are made.