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Type: Journal article
Title: Total synthesis establishes the biosynthetic pathway to the naphterpin and marinone natural products
Author: Murray, L.
Mckinnie, S.
Pepper, H.
Erni, R.
Miles, Z.
Cruickshank, M.
López-Pérez, B.
Moore, B.
George, J.
Citation: Angewandte Chemie - International Edition, 2018; 57(34):11009-11014
Publisher: Wiley
Issue Date: 2018
ISSN: 1433-7851
Statement of
Lauren A. M. Murray, Shaun M. K. McKinnie, Henry P. Pepper, Reto Erni, Zachary D. Miles, Michelle C. Cruickshank, Borja López‐Pérez, Prof. Bradley S. Moore, Jonathan H. George
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.
Keywords: Biomimetic synthesis; biosynthesis; dearomatization; meroterpenoids; total synthesis
Rights: © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
RMID: 0030095379
DOI: 10.1002/anie.201804351
Appears in Collections:Physics publications

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