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dc.contributor.authorOueis, Emilia
dc.contributor.authorJaspars, Marcel
dc.contributor.authorWestwood, Nicholas James
dc.contributor.authorNaismith, Jim
dc.date.accessioned2016-07-04T16:30:03Z
dc.date.available2016-07-04T16:30:03Z
dc.date.issued2016-05-04
dc.identifier.citationOueis , E , Jaspars , M , Westwood , N J & Naismith , J 2016 , ' Enzymatic macrocyclization of 1,2,3-triazole peptide mimetics ' , Angewandte Chemie , vol. 55 , no. 19 , pp. 5842-5845 . https://doi.org/10.1002/anie.201601564en
dc.identifier.issn0044-8249
dc.identifier.otherPURE: 241568020
dc.identifier.otherPURE UUID: f338a22a-7515-4b02-bf8c-59ff0fe6e890
dc.identifier.otherScopus: 84979493715
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424157
dc.identifier.otherWOS: 000375118500033
dc.identifier.urihttp://hdl.handle.net/10023/9076
dc.descriptionThis work was supported by the European Research Council (339367), UK Biotechnology and Biological Sciences Research Council (K015508/1), the Wellcome Trust (TripleTOF 5600 mass spectrometer (094476), the MALDI TOF-TOF Analyser (079272AIA), 700 NMR) and the EPSRC UK National Mass Spectrometry Facility at Swansea University. J.H.N. is a Royal Society Wolfson Merit Award Holder and 1000 talent scholar at Sichuan University.en
dc.description.abstractThe macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are available for their chemical macrocyclization, however, enzyme-mediated methods remain of great interest in terms of synthetic utility. To date, known macrocyclization enzymes have been shown to be active on both peptide and protein substrates. Here we show that the macrocyclization enzyme of the cyanobactin family, PatGmac, is capable of macrocyclizing substrates with one, two, or three anti-1,2,3-triazole moieties. The introduction of non-peptidic scaffolds into macrocycles is highly desirable in tuning the activity and physical properties of peptidic macrocycles. We have isolated and fully characterized nine non-natural triazole-containing cyclic peptides, a further ten molecules are also synthesized. PatGmac has now been shown to be an effective and versatile tool for the ring closure by peptide bond formation.
dc.language.isoeng
dc.relation.ispartofAngewandte Chemieen
dc.rights© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is 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://dx.doi.org/10.1002/anie.201601564en
dc.rights© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleEnzymatic macrocyclization of 1,2,3-triazole peptide mimeticsen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.description.versionPublisher PDFen
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/anie.201601564
dc.description.statusPeer revieweden


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