Cryptic Isomerization in Diterpene Biosynthesis and the Restoration of an Evolutionarily Defunct P450,Journal of the American Chemical Society

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Cryptic Isomerization in Diterpene Biosynthesis and the Restoration of an Evolutionarily Defunct P450
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-10-09 , DOI: 10.1021/jacs.3c09446
Zining Li ₁ , Baofu Xu ₁ , Tyler A Alsup ₁ , Xiuting Wei ₁ , Wenbo Ning ₁ , Daniel G Icenhour ₁ , Michelle A Ehrenberger ₁ , Ion Ghiviriga ₁ , Bao-Doan Giang ₁ , Jeffrey D Rudolf ₁

Affiliation

Biosynthetic modifications of the 6/10-bicyclic hydrocarbon skeletons of the eunicellane family of diterpenoids are unknown. We explored the biosynthesis of a bacterial trans-eunicellane natural product, albireticulone A (3), and identified a novel isomerase that catalyzes cryptic isomerization in the biosynthetic pathway. We also assigned functions of two cytochromes P450 that oxidize the eunicellane skeleton, one of which was a naturally evolved non-functional P450 that, when genetically repaired, catalyzes allylic oxidation. Finally, we described the chemical susceptibility of the trans-eunicellane skeleton to undergo Cope rearrangement to yield inseparable atropisomers.

中文翻译：

二萜生物合成中的隐蔽异构化和进化上已失效的 p450 的恢复

二萜类化合物 Eunicellane 家族的 6/10-双环烃骨架的生物合成修饰尚不清楚。我们探索了细菌反式烯单胞菌天然产物 albireticulone A （3）的生物合成，并鉴定了一种在生物合成途径中催化隐蔽异构化的新型异构酶。我们还分配了两种细胞色素 P450 的功能，它们会氧化 eunicellane 骨架，其中一种是自然进化的非功能性 P450，当基因修复时，它会催化烯丙基氧化。最后，我们描述了反式单胞菌骨架发生 Cope 重排以产生不可分离的促异构体的化学敏感性。

更新日期：2023-10-09

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