Stereochemical Assignment of the Protein-Protein Interaction Inhibitor JBIR-22 by Total Synthesis
| Autor: | Healy, Alan, Izumikawa, Miho, Slawin, Alexandra Martha Zoya, Shin-ya, Kazuo, Westwood, Nicholas James |
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| Přispěvatelé: | EPSRC, University of St Andrews. School of Chemistry, University of St Andrews. EaSTCHEM, University of St Andrews. Biomedical Sciences Research Complex |
| Rok vydání: | 2015 |
| Předmět: |
Proteasome Endopeptidase Complex
Tetrahydronaphthalenes natural products Molecular Conformation Tetramic acids Stereochemie Total synthesis Zuschrift Naturstoffe Glutamates Stereochemistry QD Protein Interaction Domains and Motifs Amino Acids total synthesis Natural products Tetraminsäuren tetramic acids Biological Products stereochemistry DAS Nichtnatürliche Aminosäuren Stereoisomerism Zuschriften General Medicine QD Chemistry Totalsynthese Communications Pyrrolidinones Unnatural amino acids unnatural amino acids |
| Zdroj: | Angewandte Chemie (International Ed. in English) Angewandte Chemie (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 0044-8249 |
| DOI: | 10.1002/ange.201411141 |
| Popis: | The authors acknowledge the EPSRC and Cancer Research UK (CRUK Grant No. C21383/A6950) for funding this research. 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. Publisher PDF |
| Databáze: | OpenAIRE |
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