Photocatalytic Functionalization of Dehydroalanine-Derived Peptides in Batch and Flow

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dc.contributor.authorKaplaneris, Nikolaos
dc.contributor.authorAkdeniz, Merve
dc.contributor.authorFillols, Méritxell
dc.contributor.authorArrighi, Francesca
dc.contributor.authorRaymenant, Fabian
dc.contributor.authorSanil, Gana
dc.contributor.authorGryko, Daniel T.
dc.contributor.authorNoël, Timothy
dc.contributor.organizationVan’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam
dc.contributor.organizationDepartment of Drug Chemistry and Technologies Sapienza, University of Rome
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.date.accessioned2024-09-02T12:08:24Z
dc.date.available2024-09-02T12:08:24Z
dc.date.issued2024
dc.description.abstractUnnatural amino acids, and their synthesis by the late-stage functionalization (LSF) of peptides, play a crucial role in areas such as drug design and discovery. Historically, the LSF of biomolecules has predominantly utilized traditional synthetic methodologies that exploit nucleophilic residues, such as cysteine, lysine or tyrosine. Herein, we present a photocatalytic hydroarylation process targeting the electrophilic residue dehydroalanine (Dha). This residue possesses an α,β-unsaturated moiety and can be combined with various arylthianthrenium salts, both in batch and flow reactors. Notably, the flow setup proved instrumental for efficient scale-up, paving the way for the synthesis of unnatural amino acids and peptides in substantial quantities. Our photocatalytic approach, being inherently mild, permits the diversification of peptides even when they contain sensitive functional groups. The readily available arylthianthrenium salts facilitate the seamless integration of Dha-containing peptides with a wide range of arenes, drug blueprints, and natural products, culminating in the creation of unconventional phenylalanine derivatives. The synergistic effect of the high functional group tolerance and the modular characteristic of the aryl electrophile enables efficient peptide conjugation and ligation in both batch and flow conditions.en
dc.description.sponsorshipEuropean Union H2020 under the call HORIZON-HLTH-2021-IND-07 (SusPharma, 101057430); under the Marie S. Curie Grant Agreement (CHAIR, No 860762); ERC CoG grant (FlowHAT, No. 101044355); FETopen (FLIX, No. 862179)
dc.identifier.citationAngew. Chem. Int. Ed. 2024, 63, e202403271 ; https://doi.org/10.1002/anie.202403271
dc.identifier.doi10.1002/anie.202403271
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/24795
dc.language.isoen
dc.publisherWiley
dc.rightsUznanie autorstwa 4.0 Międzynarodoween
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceAngewandte Chemie International Edition
dc.subjectlate-stage diversificationen
dc.subjectphotocatalysisen
dc.subjectflow chemistryen
dc.subjectunnatural amino acidsen
dc.subjectpeptidesen
dc.titlePhotocatalytic Functionalization of Dehydroalanine-Derived Peptides in Batch and Flowen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidSanil, Gana [0000-0001-7570-0544]
person.identifier.orcidGryko, Daniel T. [0000-0002-2146-1282]
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