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Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B.

ABSTRACT: The absolute stereochemistry of the cystargolides was determined by total synthesis. Evaluation of synthetic cystargolides and derivatives showed that the natural (2S,3R) stereochemistry is essential for activity. Moreover, benzyl esters (-)-10 and (-)-15 were found to be about 100 times more potent, and to selectively kill MCF-7 cancerous cells.

SUBMITTER: Tello-Aburto R

PROVIDER: S-EPMC4629797 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B.

Tello-Aburto Rodolfo R Hallada Liam P LP Niroula Doleshwar D Rogelj Snezna S

Organic & biomolecular chemistry 20150924 40

The absolute stereochemistry of the cystargolides was determined by total synthesis. Evaluation of synthetic cystargolides and derivatives showed that the natural (2S,3R) stereochemistry is essential for activity. Moreover, benzyl esters (-)-10 and (-)-15 were found to be about 100 times more potent, and to selectively kill MCF-7 cancerous cells. ...[more]

PMID: 26400369

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