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Biosynthesis of akaeolide and lorneic acids and annotation of type I polyketide synthase gene clusters in the genome of Streptomyces sp. NPS554.

Zhou T, Komaki H, Ichikawa N, Hosoyama A, Sato S, Igarashi Y - Mar Drugs (2015)

Bottom Line: The putative gene clusters contain all the polyketide synthase (PKS) domains necessary for assembly of the carbon skeletons.Combined with the 13C-labeling results, gene function prediction enabled us to propose biosynthetic pathways involving unusual carbon-carbon bond formation reactions.Genome analysis also indicated the presence of at least ten orphan type I PKS gene clusters that might be responsible for the production of new polyketides.

View Article: PubMed Central - PubMed

Affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan. t276001@st.pu-toyama.ac.jp.

ABSTRACT
The incorporation pattern of biosynthetic precursors into two structurally unique polyketides, akaeolide and lorneic acid A, was elucidated by feeding experiments with 13C-labeled precursors. In addition, the draft genome sequence of the producer, Streptomyces sp. NPS554, was performed and the biosynthetic gene clusters for these polyketides were identified. The putative gene clusters contain all the polyketide synthase (PKS) domains necessary for assembly of the carbon skeletons. Combined with the 13C-labeling results, gene function prediction enabled us to propose biosynthetic pathways involving unusual carbon-carbon bond formation reactions. Genome analysis also indicated the presence of at least ten orphan type I PKS gene clusters that might be responsible for the production of new polyketides.

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Predicted structures of linear products of orphan type I PKS gene clusters in Streptomyces sp. NPS554.
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marinedrugs-13-00581-f008: Predicted structures of linear products of orphan type I PKS gene clusters in Streptomyces sp. NPS554.

Mentions: In addition to akaeolide and lorneic acid clusters, eight orphan type I PKS gene clusters are present in Streptomyces sp. strain NPS554 (Supplementary Table S1). As for the six clusters completely sequenced, chemical structures of the linear products were predicted on the basis of domain organization (Figure 8) and prediction of stereochemistry of methyl and hydroxyl groups was made (Table S1). Clusters #2 and #8 were predicted to yield linear polyketides comprising of 24- and 23-carbon chain length, respectively, while the products of clusters #3 and #4 were much smaller, consisting of less than ten carbons. The structure of the product from cluster #7 was not completely predicted since one of the PKS modules lacked an AT domain. The side chains R1 and R2 could not be assigned only from the signature amino acid-sequences. Structures of the products from clusters #9 to #12 could not be predicted because these clusters were not completely sequenced. We recently isolated a new polyhydroxylated tetraene-macrolide corresponding to the product from cluster #5. The detailed structure determination will be reported in our forthcoming paper.


Biosynthesis of akaeolide and lorneic acids and annotation of type I polyketide synthase gene clusters in the genome of Streptomyces sp. NPS554.

Zhou T, Komaki H, Ichikawa N, Hosoyama A, Sato S, Igarashi Y - Mar Drugs (2015)

Predicted structures of linear products of orphan type I PKS gene clusters in Streptomyces sp. NPS554.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4306953&req=5

marinedrugs-13-00581-f008: Predicted structures of linear products of orphan type I PKS gene clusters in Streptomyces sp. NPS554.
Mentions: In addition to akaeolide and lorneic acid clusters, eight orphan type I PKS gene clusters are present in Streptomyces sp. strain NPS554 (Supplementary Table S1). As for the six clusters completely sequenced, chemical structures of the linear products were predicted on the basis of domain organization (Figure 8) and prediction of stereochemistry of methyl and hydroxyl groups was made (Table S1). Clusters #2 and #8 were predicted to yield linear polyketides comprising of 24- and 23-carbon chain length, respectively, while the products of clusters #3 and #4 were much smaller, consisting of less than ten carbons. The structure of the product from cluster #7 was not completely predicted since one of the PKS modules lacked an AT domain. The side chains R1 and R2 could not be assigned only from the signature amino acid-sequences. Structures of the products from clusters #9 to #12 could not be predicted because these clusters were not completely sequenced. We recently isolated a new polyhydroxylated tetraene-macrolide corresponding to the product from cluster #5. The detailed structure determination will be reported in our forthcoming paper.

Bottom Line: The putative gene clusters contain all the polyketide synthase (PKS) domains necessary for assembly of the carbon skeletons.Combined with the 13C-labeling results, gene function prediction enabled us to propose biosynthetic pathways involving unusual carbon-carbon bond formation reactions.Genome analysis also indicated the presence of at least ten orphan type I PKS gene clusters that might be responsible for the production of new polyketides.

View Article: PubMed Central - PubMed

Affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan. t276001@st.pu-toyama.ac.jp.

ABSTRACT
The incorporation pattern of biosynthetic precursors into two structurally unique polyketides, akaeolide and lorneic acid A, was elucidated by feeding experiments with 13C-labeled precursors. In addition, the draft genome sequence of the producer, Streptomyces sp. NPS554, was performed and the biosynthetic gene clusters for these polyketides were identified. The putative gene clusters contain all the polyketide synthase (PKS) domains necessary for assembly of the carbon skeletons. Combined with the 13C-labeling results, gene function prediction enabled us to propose biosynthetic pathways involving unusual carbon-carbon bond formation reactions. Genome analysis also indicated the presence of at least ten orphan type I PKS gene clusters that might be responsible for the production of new polyketides.

Show MeSH