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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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Incorporation of 13C-labeled precursors into akaeolide (1) and lorneic acid A (2).
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marinedrugs-13-00581-f003: Incorporation of 13C-labeled precursors into akaeolide (1) and lorneic acid A (2).

Mentions: The relative enrichment of each carbon by the incorporation of 13C-labeled precursors was determined by 13C NMR measurement (Table 1). Enrichments at C-5, C-9, C-15, C-18, and C-19 were observed by the feeding of [1-13C]acetate while C-3, C-7, C-11, and C-13 were highly enriched by [1-13C]propionate feeding (Table 1, Supplementary Figures S1 and S2). C-12 and C-15 were overlapped at 34.7 ppm in the 13C NMR spectrum, but the signal enhancement was ascribed to the incorporation of [1-13C]acetate into C-15 because the three-carbon fragment C-21/C-12/C-11 was derived from a propionate as proven by [1-13C]propionate incorporation into C-11 (Figure 3).


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)

Incorporation of 13C-labeled precursors into akaeolide (1) and lorneic acid A (2).
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-00581-f003: Incorporation of 13C-labeled precursors into akaeolide (1) and lorneic acid A (2).
Mentions: The relative enrichment of each carbon by the incorporation of 13C-labeled precursors was determined by 13C NMR measurement (Table 1). Enrichments at C-5, C-9, C-15, C-18, and C-19 were observed by the feeding of [1-13C]acetate while C-3, C-7, C-11, and C-13 were highly enriched by [1-13C]propionate feeding (Table 1, Supplementary Figures S1 and S2). C-12 and C-15 were overlapped at 34.7 ppm in the 13C NMR spectrum, but the signal enhancement was ascribed to the incorporation of [1-13C]acetate into C-15 because the three-carbon fragment C-21/C-12/C-11 was derived from a propionate as proven by [1-13C]propionate incorporation into C-11 (Figure 3).

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