Yatein衍生物的合成研究
No Thumbnail Available
Date
2021
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
依託泊苷(etoposide)用於治療多種惡性腫瘤及癌症，但製備須從鬼臼屬植物中分離(-)-鬼臼毒素((–)-podophyllotoxin)，再經由人工合成得到。(-)-鬼臼毒素的生物合成是由松柏醇(coniferyl alcohol)經多步驟的酵素催化反應。本實驗室有興趣的部分在於(–)-yatein 在 2-ODD 素作用下，進行分子內合環反應形成(-)-去氧鬼臼毒素的機制。為了探討酵素的反應機制，我們合成 7'-hydroxy yatein及(-)-yatein、(+)-yatein 作為酵素反應的受質，並確定各個產物的來源及 7'-hydroxy yatein 相對及絕對立體構形。
Etoposide can be used to treat a variety of malignant tumors and cancers. However, the production requires isolation of (–)-podophyllotoxin from the medicinal plant Podophyllum, followed by multi-step chemical synthesis. The biosynthesis of (–)- podophyllotoxin was accomplished from coniferyl alcohol via multiple enzyme catalysis. In the biosynthetic pathway of (–)-podophyllotoxin, we have been interested to establish a reasonable reaction mechanism for (–)-deoxypodophyllotoxin from yatein under 2-ODD-catalyzed oxidative cyclization. In order to explore the mechanism of enzymatic reaction, we synthesized 7'-hydroxy yatein, (-)-yatein and (+)-yatein as substrates for the enzymatic reaction. We determined the source of each product and the relative and absolute configuration of 7'-hydroxy yatein.
Etoposide can be used to treat a variety of malignant tumors and cancers. However, the production requires isolation of (–)-podophyllotoxin from the medicinal plant Podophyllum, followed by multi-step chemical synthesis. The biosynthesis of (–)- podophyllotoxin was accomplished from coniferyl alcohol via multiple enzyme catalysis. In the biosynthetic pathway of (–)-podophyllotoxin, we have been interested to establish a reasonable reaction mechanism for (–)-deoxypodophyllotoxin from yatein under 2-ODD-catalyzed oxidative cyclization. In order to explore the mechanism of enzymatic reaction, we synthesized 7'-hydroxy yatein, (-)-yatein and (+)-yatein as substrates for the enzymatic reaction. We determined the source of each product and the relative and absolute configuration of 7'-hydroxy yatein.
Description
Keywords
none, none