Involvement of Lipocalin-like CghA in Decalin-Forming Stereoselective Intramolecular [4+2] Cycloaddition

Sato, Michio; Yagishita, Fumitoshi; Mino, Takashi; Uchiyama, Nahoko; Patel, Ashay; Chooi, Yit-Heng; Goda, Yukihiro; Xu, Wei; Noguchi, Hiroshi; Yamamoto, Tsuyoshi; Hotta, Kinya; Houk, Kendall N.; Tang, Yi; Watanabe, Kenji

doi:10.1002/cbic.201500386

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Involvement of Lipocalin-like CghA in Decalin-Forming Stereoselective Intramolecular [4+2] Cycloaddition

11 2 2015
By Sato, Michio ; Yagishita, Fumitoshi ; Mino, Takashi ; ...
http://dx.doi.org/10.1002/cbic.201500386
Source: Chembiochem. 16(16):2294-2298

[PDF-720.42 KB]

English

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Alternative Title:

Chembiochem
Personal Author:

Sato, Michio ; Yagishita, Fumitoshi ; Mino, Takashi ; Uchiyama, Nahoko ; Patel, Ashay ; ... More +

Sato, Michio ; Yagishita, Fumitoshi ; Mino, Takashi ; Uchiyama, Nahoko ; Patel, Ashay ; Chooi, Yit-Heng ; Goda, Yukihiro ; Xu, Wei ; Noguchi, Hiroshi ; Yamamoto, Tsuyoshi ; Hotta, Kinya ; Houk, Kendall N. ; Tang, Yi ; Watanabe, Kenji Less -
Description:

Understanding enzymatic Diels-Alder (DA) reactions that can form complex natural product scaffolds is of considerable interest. Sch 210972 1, a potential anti-HIV fungal natural product, contains a decalin core that is proposed to form through a DA reaction. We identified the gene cluster responsible for the biosynthesis of 1 and heterologously reconstituted the biosynthetic pathway in Aspergillus nidulans to characterize the enzymes involved. Most notably, deletion of cghA resulted in a loss of stereoselective decalin core formation, yielding both an endo (1) and a diastereomeric exo adduct of the proposed DA reaction. Complementation with cghA restored the sole formation of 1. Density functional theory computation of the proposed DA reaction provided a plausible explanation of the observed pattern of product formation. Based on our study, we propose that lipocalin-like CghA is responsible for the stereoselective intramolecular [4+2] cycloaddition that forms the decalin core of 1.
Subjects:

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Article Aspergillus Nidulans Cycloaddition Cycloaddition Reaction Decalin Natural Product Density Functional Calculations Fungal Metabolite Fungal Proteins Lipocalins Molecular Conformation Naphthalenes Stereoisomerism Tetramic Acid Thermodynamics
Source:

Chembiochem. 16(16):2294-2298
Pubmed ID:

26360642
Pubmed Central ID:

PMC4915928
Document Type:

Journal Article
Funding:

1R01M097200/PHS HHSUnited States/ ; R01 GM097200/GM/NIGMS NIH HHSUnited States/ ; DP1 GM106413/GM/NIGMS NIH HHSUnited States/ ; T32GM008496/GM/NIGMS NIH HHSUnited States/ ; 1DP1M106413/DP/NCCDPHP CDC HHSUnited States/ ; ... More +

1R01M097200/PHS HHSUnited States/ ; R01 GM097200/GM/NIGMS NIH HHSUnited States/ ; DP1 GM106413/GM/NIGMS NIH HHSUnited States/ ; T32GM008496/GM/NIGMS NIH HHSUnited States/ ; 1DP1M106413/DP/NCCDPHP CDC HHSUnited States/ ; T32 GM008496/GM/NIGMS NIH HHSUnited States/ ; R01 GM085128/GM/NIGMS NIH HHSUnited States/ Less -
Volume:

16
Issue:

16
Collection(s):

CDC Public Access
Main Document Checksum:

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urn:sha256:b3fb4526f50b526d379c96795d8c0443dadf4d48dfcc15d3ca28fa5a48077c4e
Download URL:

https://stacks.cdc.gov/view/cdc/40002/cdc_40002_DS1.pdf
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