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Synthesis and cell cycle inhibition of the peptide enamide natural products terpeptin and the aspergillamides |
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| Authors: | Shun SuHideaki Kakeya Hiroyuki OsadaJohn A Porco Jr |
| Institution: | a Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215-2507, USA b Antibiotics Laboratory, RIKEN Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan |
| Abstract: | Total syntheses of the peptide enamide natural products terpeptin and aspergillamides A and B are reported. An oxidative decarboxylation-elimination protocol is employed to construct the indolic enamide moiety. Unambiguous stereochemical assignment of (−)-terpeptin is accomplished by synthesis of all possible stereochemical analogues. Select compounds have been evaluated in cell cycle inhibitor assays which show that the natural amino acid configuration of terpeptin has the most potent inhibitory activity. |
| Keywords: | indolic enamide terpeptin aspergillamides oxidative decarboxylation-elimination cell cycle inhibitor peptide |
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