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

被引：41

作者：

Murray, Lauren A. M. ^{[1
]}

McKinnie, Shaun M. K. ^{[2
,3
]}

Pepper, Henry P. ^{[1
]}

Erni, Reto ^{[2
,3
]}

Miles, Zachary D. ^{[2
,3
]}

Cruickshank, Michelle C. ^{[1
]}

Lopez-Perez, Borja ^{[1
]}

Moore, Bradley S. ^{[2
,3
]}

George, Jonathan H. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

[2] Univ Calif San Diego, Ctr Marine Biotechnol & Biomed, Scripps Inst Oceanog, La Jolla, CA 92093 USA

[3] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 34期

基金：

美国国家卫生研究院; 加拿大自然科学与工程研究理事会; 澳大利亚研究理事会;

关键词：

biomimetic synthesis; biosynthesis; dearomatization; meroterpenoids; total synthesis; VANADIUM-DEPENDENT CHLOROPEROXIDASES; BIOMIMETIC SYNTHESIS; STREPTOMYCES SP; STRUCTURAL ELUCIDATION; ACID BIOSYNTHESIS; NAPHTHOQUINONES; MEROCHLORINS; ANTIBIOTICS; MICROORGANISMS; REARRANGEMENT;

D O I：

10.1002/anie.201804351

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：11009 / 11014

页数：6

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