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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.


a) Oxidative cyclisation is a key step in the biosynthesis of spirobenzofuranes 189, 192 and 193. b) Mechanism of the proposed cytochrome P450-catalysed stereospecific radical coupling in the biosynthesis of griseofulvin (193). CP: chloroperoxidase; SO: sulochrin oxidase; DHO: dihydrogeodin oxidase [157–159].
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C26: a) Oxidative cyclisation is a key step in the biosynthesis of spirobenzofuranes 189, 192 and 193. b) Mechanism of the proposed cytochrome P450-catalysed stereospecific radical coupling in the biosynthesis of griseofulvin (193). CP: chloroperoxidase; SO: sulochrin oxidase; DHO: dihydrogeodin oxidase [157–159].

Mentions: Grisanes. Many fungal spirobenzofuranones contain the grisane (191) moiety as the central structural motif (Scheme 26). The spiro linkage between the B and C rings is installed by oxidative phenol coupling starting from type II-PKS-derived anthraquinone precursors [155].


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
a) Oxidative cyclisation is a key step in the biosynthesis of spirobenzofuranes 189, 192 and 193. b) Mechanism of the proposed cytochrome P450-catalysed stereospecific radical coupling in the biosynthesis of griseofulvin (193). CP: chloroperoxidase; SO: sulochrin oxidase; DHO: dihydrogeodin oxidase [157–159].
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C26: a) Oxidative cyclisation is a key step in the biosynthesis of spirobenzofuranes 189, 192 and 193. b) Mechanism of the proposed cytochrome P450-catalysed stereospecific radical coupling in the biosynthesis of griseofulvin (193). CP: chloroperoxidase; SO: sulochrin oxidase; DHO: dihydrogeodin oxidase [157–159].
Mentions: Grisanes. Many fungal spirobenzofuranones contain the grisane (191) moiety as the central structural motif (Scheme 26). The spiro linkage between the B and C rings is installed by oxidative phenol coupling starting from type II-PKS-derived anthraquinone precursors [155].

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.