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Cryptic Isomerization in Diterpene Biosynthesis and the Restoration of an Evolutionarily Defunct P450
Open accessPublished version of a preprint
Abstract
Biosynthetic modifications of the 6/10-bicyclic hydrocarbon skeletons of the eunicellane family of diterpenoids are un-known. We explored the biosynthesis of a bacterial trans-eunicellane natural product, albireticulone A (3), and identified a novel isomerase that catalyzes a cryptic isomerization in the biosynthetic pathway. We also assigned functions of two cyto-chromes 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 describe the chemical susceptibility of the trans-eunicellane skeleton to undergo Cope rearrangement to yield inseparable atropisomers.
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Highly accurate protein structure prediction with AlphaFold
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Metadata
- Authors
- Li, Z., Xu, B., Alsup, T. A., Wei, X., Ning, W., Icenhour, D. G., Ehrenberger, M. A., Ghiviriga, I., Giang, B.-D., & Rudolf, J. D.
- Affiliations
- University of Florida (US)
- Corresponding author
- Rudolf, Jeffrey D.
- ORCID
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2023-10-09
- Volume
- 145
- Issue
- 41
- Pages
- 22361-22365
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- PMC
- PMC11209839
- OpenAlex
- W4387442138
- Cited by
- 19
- References
- 1
- Citations by year
- 2026: 3 · 2025: 8 · 2024: 6 · 2023: 2
- FWCI
- 2.96
- Type
- journal article
- Language
- en
- Open access
- green
- doi.org
- Licence
- Locations
- Journal of the American Chemical Society (publishedVersion)
- ChemRxiv (acceptedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- Agence Nationale de la Recherche (ANR-17-EURE-0009)
- Division of Graduate Education (DGE-2236414)
- National Institute of General Medical Sciences (GM124461, GM142574)
- University of Florida
- Topics
- Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
- Physical Sciences › Chemistry › Organic Chemistry › Bioactive Natural Diterpenoids Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Keywords
- isomerase, cytochrome P450, allylic oxidation, Cope rearrangement, atropisomers, bacterial natural products, diterpene biosynthesis
- MeSH terms
- Bacteria, Cytochrome P-450 Enzyme System, Diterpenes, Isomerism, Oxidation-Reduction
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