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

共 50 条

[41] Biocatalyst Aided Total Synthesis of Natural Products
Hattori, Hiromu
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2018, 76 (12) : 1358 - 1359
[42] Enantioselective total synthesis of epidithiodioxopiperazine natural products
DeLorbe, John E.
Jabri, Salman Y.
Mennen, Steven M.
Zhang, Fang-Li
Overman, Larry E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[43] Structural revisions of natural products by total synthesis
Maier, Martin E.
NATURAL PRODUCT REPORTS, 2009, 26 (09) : 1105 - 1124
[44] Total synthesis of biologically active natural products
Katoh, T
JOURNAL OF PESTICIDE SCIENCE, 2000, 25 (04) : 446 - 450
[45] Total Synthesis of the Leucosceptroid Family of Natural Products
Hugelshofer, Cedric L.
Magauer, Thomas
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) : 3807 - 3810
[46] Total synthesis and development of bioactive natural products
Tatsuta, Kuniaki
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2008, 84 (04): : 87 - 106
[47] Total synthesis and biological study of natural products
St Amant, Chiara
Patel, Mansi
Xing, Yalan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[48] TOTAL SYNTHESIS OF HETEROCYCLIC NATURAL-PRODUCTS
KAMETANI, T
HETEROCYCLES, 1978, 9 (10) : 1483 - 1484
[49] Total synthesis of oxacyclic macrodiolide natural products
Kang, EJ
Lee, E
CHEMICAL REVIEWS, 2005, 105 (12) : 4348 - 4378
[50] Stereoconfining macrocyclizations in the total synthesis of natural products
Zheng, Kuan
Hong, Ran
NATURAL PRODUCT REPORTS, 2019, 36 (11) : 1546 - 1575

← 1 2 3 4 5 →