Challenging Aromaticity: Revealing a Thioesterase Domain in a Fungal Nonreducing Polyketide Synthase Governing the Production of 3‑Methylene Isochromanone
Thioesterase (TE) domain exerts a great influence over the structure of the final product and TE-released nonreduced polyketides (nrPKs) retain aromaticity. 3-Methylene isochromanones are lactones with a unique olefin at C3 that disrupts the aromaticity, whose biosynthetic details are speculative. O...
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| Veröffentlicht in: | Organic letters 2024-08, Vol.26 (30), p.6303-6308 |
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| creator | Bai, Guitao Li, Dan Wang, Yi Yi, Jiale Xu, Kangping Wang, Wenxuan Li, Jing Tan, Guishan Yu, Xia |
| description | Thioesterase (TE) domain exerts a great influence over the structure of the final product and TE-released nonreduced polyketides (nrPKs) retain aromaticity. 3-Methylene isochromanones are lactones with a unique olefin at C3 that disrupts the aromaticity, whose biosynthetic details are speculative. Our study unveils the complete biosynthesis of ascochin, in which the construction of the 3-methylene isochromanone backbone is achieved by a nonreducing polyketide synthase (nrPKS) alone and two subsequent oxidations are involved. Intriguingly, the TEAscD serves as a gatekeeper to direct the product release toward formation of nonaromatic 3-methylene isochromanone, rather than the typical aromatic product. |
| doi_str_mv | 10.1021/acs.orglett.4c01193 |
| format | Article |
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Lett</addtitle><date>2024-08-02</date><risdate>2024</risdate><volume>26</volume><issue>30</issue><spage>6303</spage><epage>6308</epage><pages>6303-6308</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>Thioesterase (TE) domain exerts a great influence over the structure of the final product and TE-released nonreduced polyketides (nrPKs) retain aromaticity. 3-Methylene isochromanones are lactones with a unique olefin at C3 that disrupts the aromaticity, whose biosynthetic details are speculative. Our study unveils the complete biosynthesis of ascochin, in which the construction of the 3-methylene isochromanone backbone is achieved by a nonreducing polyketide synthase (nrPKS) alone and two subsequent oxidations are involved. 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| source | MEDLINE; American Chemical Society Journals |
| subjects | Molecular Structure Oxidation-Reduction Polyketide Synthases - chemistry Polyketide Synthases - metabolism Polyketides - chemistry Polyketides - metabolism Thiolester Hydrolases - chemistry Thiolester Hydrolases - metabolism |
| title | Challenging Aromaticity: Revealing a Thioesterase Domain in a Fungal Nonreducing Polyketide Synthase Governing the Production of 3‑Methylene Isochromanone |
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