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Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

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ABSTRACT

This review highlights the biosynthesis of heterocycles in polyketide natural products with a focus on oxygen and nitrogen-containing heterocycles with ring sizes between 3 and 6 atoms. Heterocycles are abundant structural elements of natural products from all classes and they often contribute significantly to their biological activity. Progress in recent years has led to a much better understanding of their biosynthesis. In this context, plenty of novel enzymology has been discovered, suggesting that these pathways are an attractive target for future studies.

No MeSH data available.


Schematic description of the cyclisation reaction catalysed by TE domains. In most cases, the nucleophile “X” represents oxygen or nitrogen leading to lactones or lactams, respectively.
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C1: Schematic description of the cyclisation reaction catalysed by TE domains. In most cases, the nucleophile “X” represents oxygen or nitrogen leading to lactones or lactams, respectively.

Mentions: Among these domains, only TE domains participate in cyclisation reactions as part of their standard catalytic repertoire (Scheme 1). They transacylate the thioester of a PKS-bound polyketide onto a nucleophile. If the nucleophile is water, this leads to carboxylic acids. The reactions of backbone hydroxy groups or amines consequently give lactones and lactams. TE domains mostly form macrocycles or more rarely medium-sized and small cycles with defined size.


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Schematic description of the cyclisation reaction catalysed by TE domains. In most cases, the nucleophile “X” represents oxygen or nitrogen leading to lactones or lactams, respectively.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979870&req=5

C1: Schematic description of the cyclisation reaction catalysed by TE domains. In most cases, the nucleophile “X” represents oxygen or nitrogen leading to lactones or lactams, respectively.
Mentions: Among these domains, only TE domains participate in cyclisation reactions as part of their standard catalytic repertoire (Scheme 1). They transacylate the thioester of a PKS-bound polyketide onto a nucleophile. If the nucleophile is water, this leads to carboxylic acids. The reactions of backbone hydroxy groups or amines consequently give lactones and lactams. TE domains mostly form macrocycles or more rarely medium-sized and small cycles with defined size.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

This review highlights the biosynthesis of heterocycles in polyketide natural products with a focus on oxygen and nitrogen-containing heterocycles with ring sizes between 3 and 6 atoms. Heterocycles are abundant structural elements of natural products from all classes and they often contribute significantly to their biological activity. Progress in recent years has led to a much better understanding of their biosynthesis. In this context, plenty of novel enzymology has been discovered, suggesting that these pathways are an attractive target for future studies.

No MeSH data available.