Files in this item
Derivatisable cyanobactin analogues : a semisynthetic approach
Item metadata
dc.contributor.author | Oueis, Emilia | |
dc.contributor.author | Adamson, Catherine S | |
dc.contributor.author | Mann, Greg | |
dc.contributor.author | Ludewig, Hannes | |
dc.contributor.author | Naismith, Jim | |
dc.contributor.author | Redpath, Philip | |
dc.contributor.author | Migaud, Marie | |
dc.contributor.author | Westwood, Nicholas James | |
dc.contributor.author | Naismith, Jim | |
dc.date.accessioned | 2015-12-11T16:10:02Z | |
dc.date.available | 2015-12-11T16:10:02Z | |
dc.date.issued | 2015-12-14 | |
dc.identifier | 229918479 | |
dc.identifier | fd297861-d83d-4cb1-a8d1-99b526715d52 | |
dc.identifier | 84956782508 | |
dc.identifier | 000367720300015 | |
dc.identifier.citation | Oueis , E , Adamson , C S , Mann , G , Ludewig , H , Naismith , J , Redpath , P , Migaud , M , Westwood , N J & Naismith , J 2015 , ' Derivatisable cyanobactin analogues : a semisynthetic approach ' , ChemBioChem , vol. 16 , no. 18 , pp. 2646-2650 . https://doi.org/10.1002/cbic.201500494 | en |
dc.identifier.issn | 1439-4227 | |
dc.identifier.other | ORCID: /0000-0003-0630-0138/work/56424210 | |
dc.identifier.other | ORCID: /0000-0001-7673-5212/work/60630455 | |
dc.identifier.uri | https://hdl.handle.net/10023/7908 | |
dc.description | This work was supported by the European Research Council (339367), UK Biotechnology and Biological Sciences Research Council (K015508/1) and the Wellcome Trust (Triple TOF 5600 mass spectrometer (094476), the MALDI TOF-TOF Analyser (079272AIA), 700 NMR and supported G.M. (097831)). J.H.N. is a Royal Society Wolfson Merit Award Holder and 1000 talent scholar at Sichuan University. | en |
dc.description.abstract | Many natural cyclic peptides have potent and potentially useful biological activities. Their use as therapeutic starting points is often limited by the quantities available, the lack of known biological targets and the practical limits on diversification to fine-tune their properties. We report the use of enzymes from the cyanobactin family to heterocyclise and macrocyclise chemically synthesised substrates so as to allow larger-scale syntheses and better control over derivatisation. We have made cyclic peptides containing orthogonal reactive groups, azide or dehydroalanine, that allow chemical diversification, including the use of fluorescent labels that can help in target identification. We show that the enzymes are compatible and efficient with such unnatural substrates. The combination of chemical synthesis and enzymatic transformation could help renew interest in investigating natural cyclic peptides with biological activity, as well as their unnatural analogues, as therapeutics. | |
dc.format.extent | 2685053 | |
dc.language.iso | eng | |
dc.relation.ispartof | ChemBioChem | en |
dc.subject | Click chemistry | en |
dc.subject | Cyclic peptides | en |
dc.subject | Enzymatic reaction | en |
dc.subject | Macrocyclisation | en |
dc.subject | Patellamides | en |
dc.subject | QH301 Biology | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QH301 | en |
dc.subject.lcc | QD | en |
dc.title | Derivatisable cyanobactin analogues : a semisynthetic approach | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Wellcome Trust | en |
dc.contributor.sponsor | BBSRC | en |
dc.contributor.sponsor | The Wellcome Trust | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. School of Biology | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/cbic.201500494 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/cbic.201500494/suppinfo | en |
dc.identifier.grantnumber | 097831/z/11/z | en |
dc.identifier.grantnumber | BB/K015508/1 | en |
dc.identifier.grantnumber | 094476/Z/10/Z | en |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.