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Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products
- Murray, Lauren AM;
- McKinnie, Shaun MK;
- Pepper, Henry P;
- Erni, Reto;
- Miles, Zachary D;
- Cruickshank, Michelle C;
- López‐Pérez, Borja;
- Moore, Bradley S;
- George, Jonathan H
Published Web Location
https://doi.org/10.1002/anie.201804351Abstract
The naphterpins and marinones are naphthoquinone meroterpenoids with an unusual aromatic oxidation pattern that is biosynthesized from 1,3,6,8-tetrahydroxynaphthalene (THN). We propose that cryptic halogenation of THN derivatives by vanadium-dependent chloroperoxidase (VCPO) enzymes is key to this biosynthetic pathway, despite the absence of chlorine in these natural products. This speculation inspired a total synthesis to mimic the naphterpin/marinone biosynthetic pathway. In validation of this biogenetic hypothesis, two VCPOs were discovered that interconvert several of the proposed biosynthetic intermediates.
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