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dc.contributor.authorHoussen, W.E.
dc.contributor.authorBent, A.F.
dc.contributor.authorMcEwan, A.R.
dc.contributor.authorPieiller, N.
dc.contributor.authorTabudravu, J.
dc.contributor.authorKoehnke, J.
dc.contributor.authorMann, G.
dc.contributor.authorAdaba, R.I.
dc.contributor.authorThomas, L.
dc.contributor.authorHawas, U.W.
dc.contributor.authorLiu, H.
dc.contributor.authorSchwarz-Linek, U.
dc.contributor.authorSmith, M.C.M.
dc.contributor.authorNaismith, J.H.
dc.contributor.authorJaspars, M.
dc.date.accessioned2015-01-06T11:31:01Z
dc.date.available2015-01-06T11:31:01Z
dc.date.issued2014-12-15
dc.identifier161261960
dc.identifierd27dd74b-a332-4f7a-8dde-97e16ac1391c
dc.identifier84917710839
dc.identifier000346484400040
dc.identifier.citationHoussen , W E , Bent , A F , McEwan , A R , Pieiller , N , Tabudravu , J , Koehnke , J , Mann , G , Adaba , R I , Thomas , L , Hawas , U W , Liu , H , Schwarz-Linek , U , Smith , M C M , Naismith , J H & Jaspars , M 2014 , ' An efficient method for the in vitro production of Azol(in)e-based cyclic peptides ' , Angewandte Chemie International Edition , vol. 53 , no. 51 , pp. 14171-14174 . https://doi.org/10.1002/anie.201408082en
dc.identifier.issn1433-7851
dc.identifier.otherORCID: /0000-0003-0526-223X/work/40714975
dc.identifier.urihttps://hdl.handle.net/10023/5970
dc.descriptionThis paper was funded by: Funded Access, Leverhulme Trust. Grant Number: RPG-2012-504, TSB. Grant Number: 131181, ERC. Grant Number: 339367, and BBSRC. Grant Number: BB/K015508/1en
dc.description.abstractHeterocycle-containing cyclic peptides are promising scaffolds for the pharmaceutical industry but their chemical synthesis is very challenging. A new universal method has been devised to prepare these compounds by using a set of engineered marine-derived enzymes and substrates obtained from a family of ribosomally produced and post-translationally modified peptides called the cyanobactins. The substrate precursor peptide is engineered to have a non-native protease cleavage site that can be rapidly cleaved. The other enzymes used are heterocyclases that convert Cys or Cys/Ser/Thr into their corresponding azolines. A macrocycle is formed using a macrocyclase enzyme, followed by oxidation of the azolines to azoles with a specific oxidase. The work is exemplified by the production of 17 macrocycles containing 6-9 residues representing 11 out of the 20 canonical amino acids.
dc.format.extent4
dc.format.extent467157
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
dc.subjectCyanobactinsen
dc.subjectCyclic peptidesen
dc.subjectBiosynthesisen
dc.subjectPatellamidesen
dc.subjectRibosomal peptidesen
dc.subjectQD Chemistryen
dc.subjectSDG 14 - Life Below Wateren
dc.subject.lccQDen
dc.titleAn efficient method for the in vitro production of Azol(in)e-based cyclic peptidesen
dc.typeJournal articleen
dc.contributor.sponsorBBSRCen
dc.contributor.sponsorBBSRCen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. School of Biologyen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.1002/anie.201408082
dc.description.statusPeer revieweden
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/anie.201408082/suppinfoen
dc.identifier.grantnumberBB/K015508/1en
dc.identifier.grantnumberBB/L004380/1en


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