Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products.

ABSTRACT: 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.

SUBMITTER: Murray LAM 

PROVIDER: S-EPMC6248334 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature