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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) Biosynthesis of the pyridinone tenellin (234). b) A radical mechanism was proposed for the ring-expansion reaction catalysed by TenA. c) Other fungal pyridinone-containing hybrid iPKS–NRPS natural products [178,180].
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C33: a) Biosynthesis of the pyridinone tenellin (234). b) A radical mechanism was proposed for the ring-expansion reaction catalysed by TenA. c) Other fungal pyridinone-containing hybrid iPKS–NRPS natural products [178,180].

Mentions: The backbone of the tenellins from the insect pathogen Beauveria bassiana is assembled by an iPKS–NRPS hybrid and the resulting N-β-ketoacyl-β-tyrosinyl-S-PCP intermediate 231 is cyclised by an R* domain to yield the tetramic acid pretenellin A (232, Scheme 33). Two cytochrome P450 monooxygenases then catalyse the consecutive ring expansion to the pyridinone and N-hydroxylation. TenA was annotated as the ring expandase responsible for pyridinone formation.


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
a) Biosynthesis of the pyridinone tenellin (234). b) A radical mechanism was proposed for the ring-expansion reaction catalysed by TenA. c) Other fungal pyridinone-containing hybrid iPKS–NRPS natural products [178,180].
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C33: a) Biosynthesis of the pyridinone tenellin (234). b) A radical mechanism was proposed for the ring-expansion reaction catalysed by TenA. c) Other fungal pyridinone-containing hybrid iPKS–NRPS natural products [178,180].
Mentions: The backbone of the tenellins from the insect pathogen Beauveria bassiana is assembled by an iPKS–NRPS hybrid and the resulting N-β-ketoacyl-β-tyrosinyl-S-PCP intermediate 231 is cyclised by an R* domain to yield the tetramic acid pretenellin A (232, Scheme 33). Two cytochrome P450 monooxygenases then catalyse the consecutive ring expansion to the pyridinone and N-hydroxylation. TenA was annotated as the ring expandase responsible for pyridinone formation.

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.