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Issue 19, 2020
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Evidence for enzyme catalysed intramolecular [4+2] Diels–Alder cyclization during the biosynthesis of pyrichalasin H

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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.

Graphical abstract: Evidence for enzyme catalysed intramolecular [4+2] Diels–Alder cyclization during the biosynthesis of pyrichalasin H

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Supplementary files

Article information


Submitted
10 Dec 2019
Accepted
06 Jan 2020
First published
10 Feb 2020

This article is Open Access

Chem. Commun., 2020,56, 2925-2928
Article type
Communication

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

V. Hantke, E. J. Skellam and R. J. Cox, Chem. Commun., 2020, 56, 2925
DOI: 10.1039/C9CC09590J

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