Structure of a Peptidal Antibiotic P168 Produced by Paecilomyces lilacinus (Thom) Samson |
| |
| Authors: | Akira Isogai Akinori Suzuki Shizuo Higashkawa Shimpei Kuyama Saburo Tamura |
| |
| Institution: | 1. Department of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo 113, Japan;2. Nihon Tokushu Noyaku Seizo Co. Ltd., Toyoda, Hino-shi, Tokyo 191, Japan |
| |
| Abstract: | ( + )-α-Kainic acid (1) was synthesized by starting from a building block, N-Boc-3-acetoxyallylglycine ethyl ester (2). The key intermediate, a methyl 4-(tert-butoxycarbonyl)prenylamino]-5-hydroxy-2-pentenoate derivative (9), was prepared from 2 in eight synthetic steps. After converting 10 into a methyl ester (11), intramolecular ene-carbocyclization of 11 gave a pyrrolidine derivative (12), which was converted to 1 in a moderate yield. |
| |
| Keywords: | biotin 7-keto-8-aminopelargonic acid synthase thermophilic enzyme α-oxoamine synthase family 2-amino-3-ketobutyrate CoA ligase |
|
|
