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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.


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A Dieckmann condensation leads to the formation of a 3-acyl-4-hydroxypyridin-2-one 227 and removes the biosynthetic precursor from the PKS–NRPS hybrid assembly line during kirromycin (228) biosynthesis [174].
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C32: A Dieckmann condensation leads to the formation of a 3-acyl-4-hydroxypyridin-2-one 227 and removes the biosynthetic precursor from the PKS–NRPS hybrid assembly line during kirromycin (228) biosynthesis [174].

Mentions: 2.1.3 Dieckmann condensation: Actinomycete-derived pyridinone natural products are formed in a similar fashion as tetramates (see chapter 2.2.1) [174]. Elaborate polyketide intermediates are condensed to the amine functionality of a PCP-bound β-alanine on the terminal module of a PKS–NRPS assembly line (Scheme 32). The resulting N-β-ketoacyl-β-alanyl-S-PCP (3-(3-oxoalkylamido)propanoyl-S-PCP, 225) is then processed by a Dieckmann cyclase to give the heterocycle 226 that tautomerises to the 4-hydroxy-3-acylpyridin-2-one (227) [174].


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
A Dieckmann condensation leads to the formation of a 3-acyl-4-hydroxypyridin-2-one 227 and removes the biosynthetic precursor from the PKS–NRPS hybrid assembly line during kirromycin (228) biosynthesis [174].
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C32: A Dieckmann condensation leads to the formation of a 3-acyl-4-hydroxypyridin-2-one 227 and removes the biosynthetic precursor from the PKS–NRPS hybrid assembly line during kirromycin (228) biosynthesis [174].
Mentions: 2.1.3 Dieckmann condensation: Actinomycete-derived pyridinone natural products are formed in a similar fashion as tetramates (see chapter 2.2.1) [174]. Elaborate polyketide intermediates are condensed to the amine functionality of a PCP-bound β-alanine on the terminal module of a PKS–NRPS assembly line (Scheme 32). The resulting N-β-ketoacyl-β-alanyl-S-PCP (3-(3-oxoalkylamido)propanoyl-S-PCP, 225) is then processed by a Dieckmann cyclase to give the heterocycle 226 that tautomerises to the 4-hydroxy-3-acylpyridin-2-one (227) [174].

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.


Related in: MedlinePlus