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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.


Dieckmann cyclases catalyse tetramate or 2-pyridone formation in the biosynthesis of, for example, tirandamycin B (281), streptolyldigin (282), α-lipomycin (283) and kirromycin (228), respectively. DCy: Dieckmann cyclase. Adapted from [174].
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C40: Dieckmann cyclases catalyse tetramate or 2-pyridone formation in the biosynthesis of, for example, tirandamycin B (281), streptolyldigin (282), α-lipomycin (283) and kirromycin (228), respectively. DCy: Dieckmann cyclase. Adapted from [174].

Mentions: Surprisingly, in some actinomycete-derived tetramic acid-containing natural products, R* or TE domains as well as PyrD3/PyrD4-homologs are absent in the respective gene clusters. On the contrary, recent in vitro studies revealed conserved dedicated Dieckmann cyclases as catalysts in the biosynthetic pathways towards tirandamycin B (281), streptoylydigin (282) and α-lipomycin (283), respectively (Scheme 40) [174].


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Dieckmann cyclases catalyse tetramate or 2-pyridone formation in the biosynthesis of, for example, tirandamycin B (281), streptolyldigin (282), α-lipomycin (283) and kirromycin (228), respectively. DCy: Dieckmann cyclase. Adapted from [174].
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C40: Dieckmann cyclases catalyse tetramate or 2-pyridone formation in the biosynthesis of, for example, tirandamycin B (281), streptolyldigin (282), α-lipomycin (283) and kirromycin (228), respectively. DCy: Dieckmann cyclase. Adapted from [174].
Mentions: Surprisingly, in some actinomycete-derived tetramic acid-containing natural products, R* or TE domains as well as PyrD3/PyrD4-homologs are absent in the respective gene clusters. On the contrary, recent in vitro studies revealed conserved dedicated Dieckmann cyclases as catalysts in the biosynthetic pathways towards tirandamycin B (281), streptoylydigin (282) and α-lipomycin (283), respectively (Scheme 40) [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.