Fragrant Venezuelaenes A and B with A 5-5-6-7 Tetracyclic Skeleton: Discovery, Biosynthesis, and Mechanisms of Central Catalysts
| 发表年度： |
2020 |
| 期： |
10 |
| 卷： |
10 |
| 页： |
5846-5851 |
| 摘要： |
A cryptic terpenoid biosynthetic gene cluster yen was characterized from the model actinomycetic strain Streptomyces venezuelae ATCC 15439 through a genome mining approach. Silent gene activation and heterologous expression of ven led to the discovery of two diterpene metabolites venezuelaene A (1) and B (2, 5-oxo-venezuelaene A), both of which bear a 5-5-6-7 tetracyclic skeleton and show fragrance. A class I diterpene synthase VenA with an atypical (DSFVSD120)-D-115 motif was revealed to catalyze the cyclization of geranylgeranyl pyrophosphate (GGPP) generated by the GGPP synthase VenD, giving rise to 1. The unique cyclization mechanism was elucidated by C-13-tracer NMR experiments. The oxidative transformation of 1 into 2 was also characterized to be mediated by the cytochrome P450 enzyme VenC. |
| 刊物名称： |
ACS CATALYSIS |
| 影响因子： |
12.221 |
