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dc.contributor.authorGarcía-Pindado, Júlia
dc.contributor.authorWillemse, Tom
dc.contributor.authorGoss, Rebecca
dc.contributor.authorMaes, Bert U. W.
dc.contributor.authorGiralt, Ernest
dc.contributor.authorBallet, Steven
dc.contributor.authorTeixidó, Meritxell
dc.date.accessioned2019-03-12T00:38:17Z
dc.date.available2019-03-12T00:38:17Z
dc.date.issued2018-03-12
dc.identifier.citationGarcía-Pindado , J , Willemse , T , Goss , R , Maes , B U W , Giralt , E , Ballet , S & Teixidó , M 2018 , ' Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides ' , Biopolymers , vol. Early View . https://doi.org/10.1002/bip.23112en
dc.identifier.issn1097-0282
dc.identifier.otherPURE: 252533136
dc.identifier.otherPURE UUID: ef05c9b9-9a60-493b-94a9-7bfc27e27dd5
dc.identifier.otherBibtex: urn:a0f371fb4fe662bef7a1395d178a070a
dc.identifier.otherScopus: 85043504332
dc.identifier.otherWOS: 000449145100008
dc.identifier.urihttp://hdl.handle.net/10023/17256
dc.descriptionThis work was supported by MINECO-FEDER (BIO2016–75327-R) and the Generalitat de Catalunya (XRB and 2014-SGR-521). Júlia García was supported by an FPU grant (AP2012–6464). IRB Barcelona is the recipient of a Severo Ochoa Award of Excellence from MINECO. The IWT Flanders and Janssen Pharmaceutica are thanked for providing financial support of T.W. B.U.W.M ad S.B. thank the Research Foundation Flanders (FWO Vlaanderen; Scientific Research Network (WOG)).en
dc.description.abstractWhile revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on-resin Suzuki-Miyaura cross-coupling reactions.
dc.language.isoeng
dc.relation.ispartofBiopolymersen
dc.rights© 2018, Wiley Periodicals, Inc. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/bip.23112en
dc.subjectBiostabilityen
dc.subjectBrominationen
dc.subjectOn-resin Miyaura and Suzuki-Miyaura cross-couplingen
dc.subjectPAMPAen
dc.subjectSolid-phase peptide synthesisen
dc.subjectTryptophanen
dc.subjectQD Chemistryen
dc.subjectQH301 Biologyen
dc.subjectNDASen
dc.subject.lccQDen
dc.subject.lccQH301en
dc.titleBromotryptophans and their incorporation in cyclic and bicyclic privileged peptidesen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1002/bip.23112
dc.description.statusPeer revieweden
dc.date.embargoedUntil2019-03-12


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