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Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis

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healy2015angewandtechemiint4046.pdf (751.9Kb)
Date
23/03/2015
Author
Healy, Alan
Izumikawa, Miho
Slawin, Alexandra Martha Zoya
Shin-ya, Kazuo
Westwood, Nicholas James
Keywords
Natural products
Stereochemistry
Tetramic acids
Total synthesis
Unnatural amino acids
QD Chemistry
DAS
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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.
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
Publication
Angewandte Chemie
Status
Peer reviewed
DOI
https://doi.org/10.1002/anie.201411141
ISSN
0044-8249
Type
Journal article
Rights
Copyright 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.
Description
The authors acknowledge the EPSRC and Cancer Research UK (CRUK Grant No. C21383/A6950) for funding this research.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/6592

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