Monma Souichi, Sunazuka Toshiaki, Nagai Kenichiro, Arai Takahiro, Shiomi Kazuro, Matsui Ryosuke, Omura Satoshi
Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, Tokyo 108-8641, Japan.
Org Lett. 2006 Nov 23;8(24):5601-4. doi: 10.1021/ol0623365.
Verticilide (1) is a 24-membered cyclic depsipeptide isolated from the culture broth of Verticillium sp. FKI-1033. It inhibits ryanodine binding to ryanodine receptor (RyR) and has insecticidal activity. The stereochemistry of 2-hydroxyheptanoic acid in verticilide was elucidated by chiral HPLC analysis of the degradation product 6 and synthetic (+) and (-)-6. We also describe the practical total synthesis of verticilide. [reaction: see text].
轮枝菌素(1)是一种从轮枝菌属FKI-1033的培养液中分离得到的24元环缩肽。它能抑制ryanodine与ryanodine受体(RyR)的结合,并具有杀虫活性。通过对降解产物6以及合成的(+)-6和(-)-6进行手性高效液相色谱分析,阐明了轮枝菌素中2-羟基庚酸的立体化学结构。我们还描述了轮枝菌素的实用全合成方法。[反应:见正文]