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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.


Related in: MedlinePlus

The domain AmbDH3 from ambruticin biosynthesis catalyses the dehydration of 25 and subsequent cyclisation to tetrahydropyran 27 with high stereoselectivity [15].
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C4: The domain AmbDH3 from ambruticin biosynthesis catalyses the dehydration of 25 and subsequent cyclisation to tetrahydropyran 27 with high stereoselectivity [15].

Mentions: 1.1.1 oxa-Michael addition: The oxa-Michael addition on an α,β-unsaturated thioester intermediate leads to oxygen heterocycles along with the formation of up to two new stereocentres. Its appearance in several polyketide biosynthetic pathways was proposed for a decade based on gene cluster analysis. An in vitro characterisation of responsible catalytic units has however only recently been achieved. Two pyran-forming cyclase domains were characterised in the pederin (24) and the ambruticin (28) biosynthetic pathways (Scheme 3 and Scheme 4) [14–15].


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
The domain AmbDH3 from ambruticin biosynthesis catalyses the dehydration of 25 and subsequent cyclisation to tetrahydropyran 27 with high stereoselectivity [15].
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C4: The domain AmbDH3 from ambruticin biosynthesis catalyses the dehydration of 25 and subsequent cyclisation to tetrahydropyran 27 with high stereoselectivity [15].
Mentions: 1.1.1 oxa-Michael addition: The oxa-Michael addition on an α,β-unsaturated thioester intermediate leads to oxygen heterocycles along with the formation of up to two new stereocentres. Its appearance in several polyketide biosynthetic pathways was proposed for a decade based on gene cluster analysis. An in vitro characterisation of responsible catalytic units has however only recently been achieved. Two pyran-forming cyclase domains were characterised in the pederin (24) and the ambruticin (28) biosynthetic pathways (Scheme 3 and Scheme 4) [14–15].

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