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An efficient method for the in vitro production of Azol(in)e-based cyclic peptides
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dc.contributor.author | Houssen, W.E. | |
dc.contributor.author | Bent, A.F. | |
dc.contributor.author | McEwan, A.R. | |
dc.contributor.author | Pieiller, N. | |
dc.contributor.author | Tabudravu, J. | |
dc.contributor.author | Koehnke, J. | |
dc.contributor.author | Mann, G. | |
dc.contributor.author | Adaba, R.I. | |
dc.contributor.author | Thomas, L. | |
dc.contributor.author | Hawas, U.W. | |
dc.contributor.author | Liu, H. | |
dc.contributor.author | Schwarz-Linek, U. | |
dc.contributor.author | Smith, M.C.M. | |
dc.contributor.author | Naismith, J.H. | |
dc.contributor.author | Jaspars, M. | |
dc.date.accessioned | 2015-01-06T11:31:01Z | |
dc.date.available | 2015-01-06T11:31:01Z | |
dc.date.issued | 2014-12-15 | |
dc.identifier | 161261960 | |
dc.identifier | d27dd74b-a332-4f7a-8dde-97e16ac1391c | |
dc.identifier | 84917710839 | |
dc.identifier | 000346484400040 | |
dc.identifier.citation | Houssen , 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.201408082 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | ORCID: /0000-0003-0526-223X/work/40714975 | |
dc.identifier.uri | https://hdl.handle.net/10023/5970 | |
dc.description | This 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/K015508/1 | en |
dc.description.abstract | Heterocycle-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.extent | 4 | |
dc.format.extent | 467157 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Cyanobactins | en |
dc.subject | Cyclic peptides | en |
dc.subject | Biosynthesis | en |
dc.subject | Patellamides | en |
dc.subject | Ribosomal peptides | en |
dc.subject | QD Chemistry | en |
dc.subject | SDG 14 - Life Below Water | en |
dc.subject.lcc | QD | en |
dc.title | An efficient method for the in vitro production of Azol(in)e-based cyclic peptides | en |
dc.type | Journal article | en |
dc.contributor.sponsor | BBSRC | en |
dc.contributor.sponsor | BBSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. School of Biology | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1002/anie.201408082 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/anie.201408082/suppinfo | en |
dc.identifier.grantnumber | BB/K015508/1 | en |
dc.identifier.grantnumber | BB/L004380/1 | en |
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