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Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis
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dc.contributor.author | Healy, Alan | |
dc.contributor.author | Izumikawa, Miho | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Shin-ya, Kazuo | |
dc.contributor.author | Westwood, Nicholas James | |
dc.date.accessioned | 2015-04-29T10:01:01Z | |
dc.date.available | 2015-04-29T10:01:01Z | |
dc.date.issued | 2015-03-23 | |
dc.identifier | 161268218 | |
dc.identifier | b8e822d5-4027-41c3-898d-4dc9ba98027a | |
dc.identifier | 84922344752 | |
dc.identifier | 000351204600036 | |
dc.identifier | 25650886 | |
dc.identifier.citation | Healy , 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.201411141 | en |
dc.identifier.issn | 0044-8249 | |
dc.identifier.other | ORCID: /0000-0003-0630-0138/work/56424184 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861892 | |
dc.identifier.uri | https://hdl.handle.net/10023/6592 | |
dc.description | The authors acknowledge the EPSRC and Cancer Research UK (CRUK Grant No. C21383/A6950) for funding this research. | en |
dc.description.abstract | Recent 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.format.extent | 770035 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie | en |
dc.subject | Natural products | en |
dc.subject | Stereochemistry | en |
dc.subject | Tetramic acids | en |
dc.subject | Total synthesis | en |
dc.subject | Unnatural amino acids | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1002/anie.201411141 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/K039210/1 | en |
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