Details:

Alternative Title:
J Am Chem Soc
Publisher's site:
http://dx.doi.org/10.1021/jacs.5b07816
Personal Author:
Mao, Xu-Ming ; Zhan, Zha-Jun ; Grayson, Matthew N. ; Tang, Man-Cheng ; Xu, Wei ; ... More +
Mao, Xu-Ming ; Zhan, Zha-Jun ; Grayson, Matthew N. ; Tang, Man-Cheng ; Xu, Wei ; Li, Yong-Quan ; Yin, Wen-Bing ; Lin, Hsiao-Ching ; Chooi, Yit-Heng ; Houk, K. N. ; Tang, Yi Less -
Description:
Aurovertins are fungal polyketides that exhibit potent inhibition of adenosine triphosphate synthase. Aurovertins contain a 2,6-dioxabicyclo[3.2.1]octane ring that is proposed to be derived from a polyene precursor through regioselective oxidations and epoxide openings. In this study, we identified only four enzymes required to produce aurovertin E. The core polyketide synthase produces a polyene α-pyrone. Following pyrone O-methylation by a methyltransferase, a flavin-dependent mono-oxygenase and an epoxide hydrolase can iteratively transform the terminal triene portion of the precursor into the dioxabicyclo[3.2.1]octane scaffold. We demonstrate that a tetrahydrofuranyl polyene is the first stable intermediate in the transformation, which can undergo epoxidation and anti-Baldwin 6-endo-tet ring opening to yield the cyclic ether product. Our results further demonstrate the highly concise and efficient ways in which fungal biosynthetic pathways can generate complex natural product scaffolds.
Subject:
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Article Aurovertins Fungi Octanes Polyketides Stereoisomerism
Source:
J Am Chem Soc. 137(37):11904-11907.
Pubmed ID:
26340065
Pubmed Central ID:
PMC4903023
Document Type:
Journal Article
Funding:
DP1 GM106413/GM/NIGMS NIH HHS/United States ; R01 GM085128/GM/NIGMS NIH HHS/United States ; 1DP1GM106413/DP/NCCDPHP CDC HHS/United States ; 1R01GM085128/GM/NIGMS NIH HHS/United States
DP1 GM106413/GM/NIGMS NIH HHS/United States ; R01 GM085128/GM/NIGMS NIH HHS/United States ; 1DP1GM106413/DP/NCCDPHP CDC HHS/United States ; 1R01GM085128/GM/NIGMS NIH HHS/United States Less -
Collection(s):
CDC Public Access
Main Document Checksum:
[+]
urn:sha256:a0da26604f42c21f299143275676332f2a2791155bdcb15b0c8777d1d05c4010
Download URL:
https://stacks.cdc.gov/view/cdc/39865/cdc_39865_DS1.pdf
File Type:

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