Please use this identifier to cite or link to this item:
http://hdl.handle.net/2440/117704
Citations | ||
Scopus | Web of Science® | Altmetric |
---|---|---|
?
|
?
|
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 1521-3773 |
Statement of Responsibility: | 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 |
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.