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dc.contributor.authorHealy, Alan
dc.contributor.authorIzumikawa, Miho
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorShin-ya, Kazuo
dc.contributor.authorWestwood, Nicholas James
dc.date.accessioned2015-04-29T10:01:01Z
dc.date.available2015-04-29T10:01:01Z
dc.date.issued2015-03-23
dc.identifier.citationHealy , A , Izumikawa , M , Slawin , A M Z , Shin-ya , K & Westwood , N J 2015 , ' Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis ' Angewandte Chemie , vol. 54 , no. 13 , pp. 4046-4050 . https://doi.org/10.1002/anie.201411141en
dc.identifier.issn0044-8249
dc.identifier.otherPURE: 161268218
dc.identifier.otherPURE UUID: b8e822d5-4027-41c3-898d-4dc9ba98027a
dc.identifier.otherScopus: 84922344752
dc.identifier.otherWOS: 000351204600036
dc.identifier.otherPubMed: 25650886
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424184
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861892
dc.identifier.urihttp://hdl.handle.net/10023/6592
dc.descriptionThe authors acknowledge the EPSRC and Cancer Research UK (CRUK Grant No. C21383/A6950) for funding this research.en
dc.description.abstractRecent reports have highlighted the biological activity associated with a sub-family of the tetramic acid class of natural products. Despite the fact that members of this sub-family act as protein-protein interaction inhibitors of relevance to proteasome assembly, no synthetic work has been reported. This may be because this sub-family contains an unnatural 4,4-disubstitued glutamic acid, the synthesis of which provides a key challenge. Here we describe a highly stereoselective route to a masked form of this unnatural amino acid. This enabled the synthesis of two of the possible diastereomers of JBIR-22 and allowed its relative and absolute stereochemistry to be assigned.
dc.language.isoeng
dc.relation.ispartofAngewandte Chemieen
dc.rightsCopyright 2015 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.subjectNatural productsen
dc.subjectStereochemistryen
dc.subjectTetramic acidsen
dc.subjectTotal synthesisen
dc.subjectUnnatural amino acidsen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleStereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesisen
dc.typeJournal articleen
dc.description.versionPostprinten
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.201411141
dc.description.statusPeer revieweden


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