Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis.
Angew Chem Int Ed Engl
; 54(13): 4046-50, 2015 Mar 23.
Article
em En
| MEDLINE
| ID: mdl-25650886
ABSTRACT
Recent reports have highlighted the biological activity associated with a subfamily of the tetramic acid class of natural products. Despite the fact that members of this subfamily act as protein-protein interaction inhibitors that are of relevance to proteasome assembly, no synthetic work has been reported. This may be due to the fact that this subfamily contains an unnatural 4,4-disubstitued glutamic acid, the synthesis of which provides a key challenge. A highly stereoselective route to a masked form of this unnatural amino acid now enabled the synthesis of two of the possible diastereomers of JBIR-22 and allowed the assignment of its relative and absolute stereochemistry.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirrolidinonas
/
Tetra-Hidronaftalenos
/
Domínios e Motivos de Interação entre Proteínas
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2015
Tipo de documento:
Article