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

Autor:	Lauren A. M. Murray, Shaun M. K. McKinnie, Henry P. Pepper, Reto Erni, Zachary D. Miles, Michelle C. Cruickshank, Borja López‐Pérez, Bradley S. Moore, Jonathan H. George
Rok vydání:	2018
Předmět:	Biological Products Halogenation Terpenes 010405 organic chemistry meroterpenoids Organic Chemistry Reproducibility of Results Naphthols General Medicine 010402 general chemistry 01 natural sciences dearomatization 0104 chemical sciences Biomimetics Cyclization Chemical Sciences biomimetic synthesis biosynthesis Chloride Peroxidase total synthesis Oxidation-Reduction Naphthoquinones
Zdroj:	Angewandte Chemie (International ed. in English), vol 57, iss 34
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201804351
Popis:	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.
Databáze:	OpenAIRE
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