期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 36, 页码 14052-14056出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b06592
关键词
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资金
- CAMS Innovation Fund for Medical Sciences (CIFMS) [2017-I2M-4-004, 2018-12M-3-005]
- Drug Innovation Major Project [2018ZX09711001-006]
- NSF [CHE-1806581]
- [R01GM 124480]
Diels-Alder reactions are among the most powerful synthetic transformations to construct complex natural products. Despite that increasing of enzymatic intramolecular Diels-Alder reactions have been discovered, natural intermolecular Diels-Alderases are rarely described. Here, we report an intermolecular hetero-Diels-Alder reaction in the biosynthesis of tropolonic sesquiterpenes and functionally characterize EupfF as the first fungal intermolecular hetero-Diels-Alderase. We demonstrate that EupfF catalyzed the dehydration of a hydroxymethyl-containing tropolone (5) to generate a reactive tropolone o-quinone methide (6) and might further stereoselectively control the subsequent intermolecular hetero-Diels-Alder reaction with (1E,4E,8Z)-humulenol (8) to produce enantiomerically pure neosetophomone B (1). Our results reveal the biosynthetic pathway of 1 and expand the repertoire of activities of Diels-Alder cyclases.
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