| Autor: |
Liu, Shuai, Xu, Wen-Qiang, Di, Ying-Tong, Tang, Man-Cheng, Chen, Ding-Kang, Cao, Ming-Ming, Chang, Yao-Wen, Tang, Hong-Yu, Yuan, Chun-Mao, Yang, Jun-Bo, Zuo, Zhi-Li, Guo, Han, Xu, Zi-Fei, Zeng, Ying, Wu, Yun-Dong, Hao, Xiao-Jiang |
| Zdroj: |
SCIENCE CHINA Chemistry; 20240101, Issue: Preprints p1-9, 9p |
| Abstrakt: |
In the intricate process of natural product biosynthesis, a metabolon can enhance metabolic flux by associating sequential enzymes. A fungal metabolon, comprising of flavin-dependent monooxygenase SpeF and P450 monooxygenase SpeG, is identified in the biosynthesis of spiro polycyclic alkaloids (+)-notoamide B and its diastereomer (+)-versicolamide B. Using notoamide E as a substance, SpeF/SpeG metabolon can control the stereoselectivity of its 2,3-epoxidation, followed by hydrogen atom ion at C-17 to generate reactive epoxide tau-mA with dienyl iminium unit. Subsequently, (+)-notoamide B and (+)-versicolamide B are produced viatandem nonenzymatic inverse-electron-demand Diels-Alder reaction and semipinacol rearrangement. This provides the first example of metabolon in the biosynthesis of spiro-prenylated indole alkaloids. |
| Databáze: |
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