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Biosynthesis of Versipelostatin: Identification of an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization of Spirotetronate-Containing Polyketides
[Image: see text] Versipelostatin (VST) is an unusual 17-membered macrocyclic polyketide product that contains a spirotetronate skeleton. In this study, the entire VST biosynthetic gene cluster (vst) spanning 108 kb from Streptomyces versipellis 4083-SVS6 was identified by heterologous expression us...
| Autores principales: | , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2014
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4308742/ https://www.ncbi.nlm.nih.gov/pubmed/25551461 http://dx.doi.org/10.1021/ja510711x |
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| author | Hashimoto, Takuya Hashimoto, Junko Teruya, Kuniko Hirano, Takashi Shin-ya, Kazuo Ikeda, Haruo Liu, Hung-wen Nishiyama, Makoto Kuzuyama, Tomohisa |
| author_facet | Hashimoto, Takuya Hashimoto, Junko Teruya, Kuniko Hirano, Takashi Shin-ya, Kazuo Ikeda, Haruo Liu, Hung-wen Nishiyama, Makoto Kuzuyama, Tomohisa |
| author_sort | Hashimoto, Takuya |
| collection | PubMed |
| description | [Image: see text] Versipelostatin (VST) is an unusual 17-membered macrocyclic polyketide product that contains a spirotetronate skeleton. In this study, the entire VST biosynthetic gene cluster (vst) spanning 108 kb from Streptomyces versipellis 4083-SVS6 was identified by heterologous expression using a bacterial artificial chromosome vector. Here, we demonstrate that an enzyme, VstJ, catalyzes the stereoselective [4+2]-cycloaddition between the conjugated diene and the exocyclic olefin of a newly identified tetronate-containing intermediate to form the spirotetronate skeleton during VST biosynthesis. |
| format | Online Article Text |
| id | pubmed-4308742 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2014 |
| publisher | American Chemical
Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-43087422015-12-31 Biosynthesis of Versipelostatin: Identification of an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization of Spirotetronate-Containing Polyketides Hashimoto, Takuya Hashimoto, Junko Teruya, Kuniko Hirano, Takashi Shin-ya, Kazuo Ikeda, Haruo Liu, Hung-wen Nishiyama, Makoto Kuzuyama, Tomohisa J Am Chem Soc [Image: see text] Versipelostatin (VST) is an unusual 17-membered macrocyclic polyketide product that contains a spirotetronate skeleton. In this study, the entire VST biosynthetic gene cluster (vst) spanning 108 kb from Streptomyces versipellis 4083-SVS6 was identified by heterologous expression using a bacterial artificial chromosome vector. Here, we demonstrate that an enzyme, VstJ, catalyzes the stereoselective [4+2]-cycloaddition between the conjugated diene and the exocyclic olefin of a newly identified tetronate-containing intermediate to form the spirotetronate skeleton during VST biosynthesis. American Chemical Society 2014-12-31 2015-01-21 /pmc/articles/PMC4308742/ /pubmed/25551461 http://dx.doi.org/10.1021/ja510711x Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Hashimoto, Takuya Hashimoto, Junko Teruya, Kuniko Hirano, Takashi Shin-ya, Kazuo Ikeda, Haruo Liu, Hung-wen Nishiyama, Makoto Kuzuyama, Tomohisa Biosynthesis of Versipelostatin: Identification of an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization of Spirotetronate-Containing Polyketides |
| title | Biosynthesis
of Versipelostatin: Identification of
an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization
of Spirotetronate-Containing Polyketides |
| title_full | Biosynthesis
of Versipelostatin: Identification of
an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization
of Spirotetronate-Containing Polyketides |
| title_fullStr | Biosynthesis
of Versipelostatin: Identification of
an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization
of Spirotetronate-Containing Polyketides |
| title_full_unstemmed | Biosynthesis
of Versipelostatin: Identification of
an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization
of Spirotetronate-Containing Polyketides |
| title_short | Biosynthesis
of Versipelostatin: Identification of
an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization
of Spirotetronate-Containing Polyketides |
| title_sort | biosynthesis
of versipelostatin: identification of
an enzyme-catalyzed [4+2]-cycloaddition required for macrocyclization
of spirotetronate-containing polyketides |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4308742/ https://www.ncbi.nlm.nih.gov/pubmed/25551461 http://dx.doi.org/10.1021/ja510711x |
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