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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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Conserved steps for formation and processing in several 3-acyl-tetronate biosynthetic pathways were confirmed by in vitro studies. Tmn7a, RkC, RkF and Agg3 are ACPs. Fragments, which are established by tetronate processing are shown in red [139,141–143].
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C22: Conserved steps for formation and processing in several 3-acyl-tetronate biosynthetic pathways were confirmed by in vitro studies. Tmn7a, RkC, RkF and Agg3 are ACPs. Fragments, which are established by tetronate processing are shown in red [139,141–143].

Mentions: Tetronate cyclisation. In all tetronate clusters sequenced until now, a conserved set of genes is present that codes for a glycerate-activating FkbH-like protein, an acyl carrier protein (ACP) that intermediately carries the glycerate unit and a FabH-like protein that condenses the ACP-bound glycerate with an ACP-bound β-ketothioester in an acylation–Dieckmann condensation reaction cascade (Scheme 22) [139]. This scenario has been confirmed by partial in vivo and in vitro reconstruction of tetronomycin (Tmn, 149), RK-682 (146) and agglomerin A (147) biosynthesis [141–144]. It is however not clear, in which order the two sub-steps occur.


Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Conserved steps for formation and processing in several 3-acyl-tetronate biosynthetic pathways were confirmed by in vitro studies. Tmn7a, RkC, RkF and Agg3 are ACPs. Fragments, which are established by tetronate processing are shown in red [139,141–143].
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C22: Conserved steps for formation and processing in several 3-acyl-tetronate biosynthetic pathways were confirmed by in vitro studies. Tmn7a, RkC, RkF and Agg3 are ACPs. Fragments, which are established by tetronate processing are shown in red [139,141–143].
Mentions: Tetronate cyclisation. In all tetronate clusters sequenced until now, a conserved set of genes is present that codes for a glycerate-activating FkbH-like protein, an acyl carrier protein (ACP) that intermediately carries the glycerate unit and a FabH-like protein that condenses the ACP-bound glycerate with an ACP-bound β-ketothioester in an acylation–Dieckmann condensation reaction cascade (Scheme 22) [139]. This scenario has been confirmed by partial in vivo and in vitro reconstruction of tetronomycin (Tmn, 149), RK-682 (146) and agglomerin A (147) biosynthesis [141–144]. It is however not clear, in which order the two sub-steps occur.

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