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

^*Korrespondierende*r Autor*in für diese Arbeit

Institut für Organische Chemie

Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › 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.

Originalsprache	Englisch
Seiten (von - bis)	2925-2928
Seitenumfang	4
Fachzeitschrift	Chemical communications
Jahrgang	56
Ausgabenummer	19
DOIs	https://doi.org/10.1039/c9cc09590j https://doi.org/10.1039/c9cc09590j
Publikationsstatus	Veröffentlicht - 10 Feb. 2020

ASJC Scopus Sachgebiete

Elektronische, optische und magnetische Materialien
Keramische und Verbundwerkstoffe
Metalle und Legierungen
Werkstoffchemie
Oberflächen, Beschichtungen und Folien
Allgemeine Chemie
Katalyse

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10.1039/c9cc09590jLizenz: CC BY-NC 3.0 DE
10.1039/c9cc09590j

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Link zur Publikation in Scopus

Mass Directed Auto Purification System with DAD and ELSD detectors
Cox, R. J. (Projektleiter*in (Principal Investigator))
10 Juli 2014 → 30 Juni 2015
Projekt: Forschung

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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.",

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month = feb,

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doi = "10.1039/c9cc09590j",

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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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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

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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

ASJC Scopus Sachgebiete

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Andere Dateien und Links

Projekte

Mass Directed Auto Purification System with DAD and ELSD detectors

Dieses zitieren