Total synthesis of narbonolide and biotransformation to pikromycin |
| |
Authors: | Venkatraman Lakshmanan Salomon Christine E Sherman David H Fecik Robert A |
| |
Institution: | Department of Medicinal Chemistry, 8-101 WDH, University of Minnesota, Minneapolis, Minnesota 55455-0353, USA. |
| |
Abstract: | An improved total synthesis of narbonolide and its biotransformation to pikromycin is reported. This total synthesis utilized an intramolecular Nozaki-Hiyama-Kishi coupling that significantly improved macrocyclization yields (90-96%) and allowed for differentiation of the C3- and C5-oxidation states. A pikAI deletion mutant of Streptomyces venezuelae was used to biotransform synthetic narbonolide to pikromycin by glycosylation and oxidation in vivo. This integration of synthetic chemistry and engineered biotransformations holds great promise for the synthesis of novel macrolide analogues of biological interest. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|