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

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OriginalspracheEnglisch
Seiten (von - bis)2925-2928
Seitenumfang4
FachzeitschriftChemical communications
Jahrgang56
Ausgabenummer19
PublikationsstatusVeröffentlicht - 10 Feb. 2020

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.

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Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H. / Hantke, Verena; Skellam, Elizabeth J.; Cox, Russell J.
in: Chemical communications, Jahrgang 56, Nr. 19, 10.02.2020, S. 2925-2928.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Hantke V, Skellam EJ, Cox RJ. Evidence for enzyme catalysed intramolecular [4+2] Diels-Alder cyclization during the biosynthesis of pyrichalasin H. Chemical communications. 2020 Feb 10;56(19):2925-2928. doi: 10.1039/c9cc09590j, 10.1039/c9cc09590j
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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.",
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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.",
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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.

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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

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JO - Chemical communications

JF - Chemical communications

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