Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H

Verena Hantke; Elizabeth J. Skellam; Russell J. Cox

doi:10.1039/c9cc09590j

Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H

Verena Hantke^*
, Elizabeth J. Skellam
, Russell J. Cox

^*Corresponding author for this work

Institute of Organic Chemistry

Research output: Contribution to journal › Article › Research › peer review

Abstract

Cytochalasans are highly complex fungal metabolites which exhibit diverse biological activities. Little is known of the chemical steps involved in the construction of the tricyclic core, which consists of an octahydro-isoindole skeleton fused to a macrocyclic ring. Here, using a directed gene knockout and complementation strategy, we show that PyiF is implicated as the proposed intramolecular [4+2] Diels-Alderase required for construction of the tricyclic core of pyrichalasin H 1.

Original language	English
Pages (from-to)	2925-2928
Number of pages	4
Journal	Chemical communications
Volume	56
Issue number	19
DOIs	https://doi.org/10.1039/c9cc09590j https://doi.org/10.1039/c9cc09590j
Publication status	Published - 10 Feb 2020

Keywords

Catalysis
Cycloaddition Reaction
Fungi/genetics
Gene Knockout Techniques
Genetic Complementation Test

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
General Chemistry
Catalysis

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10.1039/c9cc09590jLicence: CC BY-NC 3.0 DE
10.1039/c9cc09590j

Cite this

@article{eda389df1c2d419fa60f1894588b7cfa,

title = "Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H",

abstract = "Cytochalasans are highly complex fungal metabolites which exhibit diverse biological activities. Little is known of the chemical steps involved in the construction of the tricyclic core, which consists of an octahydro-isoindole skeleton fused to a macrocyclic ring. Here, using a directed gene knockout and complementation strategy, we show that PyiF is implicated as the proposed intramolecular [4+2] Diels-Alderase required for construction of the tricyclic core of pyrichalasin H 1.",

keywords = "Catalysis, Cycloaddition Reaction, Fungi/genetics, Gene Knockout Techniques, Genetic Complementation Test",

author = "Verena Hantke and Skellam, \{Elizabeth J.\} and Cox, \{Russell J.\}",

note = "Funding information: This work was supported by DFG [(CO 1328/2-1, INST 187/621-1, INST 187/686-1)]. The authors also thank: Professor Marc-Henri Lebrun (UMR BIOGER INRA AgroParisTech) and Dr Didier Tharreau (CIRAD UMR BGPI) for the gift of M. grisea NI980 and useful discussions; and Chongqing Wang for assistance with identification of dihydropyriculol 22.",

year = "2020",

month = feb,

day = "10",

doi = "10.1039/c9cc09590j",

language = "English",

volume = "56",

pages = "2925--2928",

journal = "Chemical communications",

issn = "1359-7345",

publisher = "Chemical Society",

number = "19",

}

TY - JOUR

T1 - Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H

AU - Hantke, Verena

AU - Skellam, Elizabeth J.

AU - Cox, Russell J.

N1 - Funding information: This work was supported by DFG [(CO 1328/2-1, INST 187/621-1, INST 187/686-1)]. The authors also thank: Professor Marc-Henri Lebrun (UMR BIOGER INRA AgroParisTech) and Dr Didier Tharreau (CIRAD UMR BGPI) for the gift of M. grisea NI980 and useful discussions; and Chongqing Wang for assistance with identification of dihydropyriculol 22.

PY - 2020/2/10

Y1 - 2020/2/10

N2 - Cytochalasans are highly complex fungal metabolites which exhibit diverse biological activities. Little is known of the chemical steps involved in the construction of the tricyclic core, which consists of an octahydro-isoindole skeleton fused to a macrocyclic ring. Here, using a directed gene knockout and complementation strategy, we show that PyiF is implicated as the proposed intramolecular [4+2] Diels-Alderase required for construction of the tricyclic core of pyrichalasin H 1.

AB - Cytochalasans are highly complex fungal metabolites which exhibit diverse biological activities. Little is known of the chemical steps involved in the construction of the tricyclic core, which consists of an octahydro-isoindole skeleton fused to a macrocyclic ring. Here, using a directed gene knockout and complementation strategy, we show that PyiF is implicated as the proposed intramolecular [4+2] Diels-Alderase required for construction of the tricyclic core of pyrichalasin H 1.

KW - Catalysis

KW - Cycloaddition Reaction

KW - Fungi/genetics

KW - Gene Knockout Techniques

KW - Genetic Complementation Test

UR - https://www.scopus.com/pages/publications/85081079707

U2 - 10.1039/c9cc09590j

DO - 10.1039/c9cc09590j

M3 - Article

C2 - 32039410

AN - SCOPUS:85081079707

SN - 1359-7345

VL - 56

SP - 2925

EP - 2928

JO - Chemical communications

JF - Chemical communications

IS - 19

ER -

Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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Mass Directed Auto Purification System with DAD and ELSD detectors

Cite this

Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Projects

Mass Directed Auto Purification System with DAD and ELSD detectors

Cite this