Deciphering fungal metabolon coupling tandem inverse-electron-demand Diels-Alder reaction and semipinacol rearrangement for the biosynthesis of spiro polycyclic alkaloids

IF 10.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Science China Chemistry Pub Date : 2024-10-31 DOI:10.1007/s11426-024-2134-0

Shuai Liu, Wen-Qiang Xu, Ying-Tong Di, Man-Cheng Tang, Ding-Kang Chen, Ming-Ming Cao, Yao-Wen Chang, Hong-Yu Tang, Chun-Mao Yuan, Jun-Bo Yang, Zhi-Li Zuo, Han Guo, Zi-Fei Xu, Ying Zeng, Yun-Dong Wu, Xiao-Jiang Hao

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引用次数: 0

Abstract

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 via tandem 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.

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来源期刊

Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

7.30%

发文量

3787

审稿时长

2.2 months

期刊介绍： Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.