Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis
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
ISSN
0044-8249Type
Journal article
Description
The authors acknowledge the EPSRC and Cancer Research UK (CRUK Grant No. C21383/A6950) for funding this research.Collections
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