Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis
We describe the characterisation of the O-methyltransferase JerF from the late stages of jerangolid biosynthesis. JerF is the first known example of an enzyme that catalyses the formation of a non-aromatic, cyclic methylenolether. The enzyme was overexpressed in E. coli and the cell-free extracts we...
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MDPI AG
2016-10-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/11/1443 |
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| author | Steffen Friedrich Franziska Hemmerling Frederick Lindner Anna Warnke Johannes Wunderlich Gesche Berkhan Frank Hahn |
| author_facet | Steffen Friedrich Franziska Hemmerling Frederick Lindner Anna Warnke Johannes Wunderlich Gesche Berkhan Frank Hahn |
| author_sort | Steffen Friedrich |
| collection | DOAJ |
| description | We describe the characterisation of the O-methyltransferase JerF from the late stages of jerangolid biosynthesis. JerF is the first known example of an enzyme that catalyses the formation of a non-aromatic, cyclic methylenolether. The enzyme was overexpressed in E. coli and the cell-free extracts were used in bioconversion experiments. Chemical synthesis gave access to a series of substrate surrogates that covered a broad structural space. Enzymatic assays revealed a broad substrate tolerance and high regioselectivity of JerF, which makes it an attractive candidate for an application in chemoenzymatic synthesis with particular usefulness for late stage application on 4-methoxy-5,6-dihydro-2H-pyran-2-one-containing natural products. |
| first_indexed | 2024-04-14T02:01:08Z |
| format | Article |
| id | doaj.art-28b828d3cf8c4693b3cb6d85da813f9e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-14T02:01:08Z |
| publishDate | 2016-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-28b828d3cf8c4693b3cb6d85da813f9e2022-12-22T02:18:49ZengMDPI AGMolecules1420-30492016-10-012111144310.3390/molecules21111443molecules21111443Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid BiosynthesisSteffen Friedrich0Franziska Hemmerling1Frederick Lindner2Anna Warnke3Johannes Wunderlich4Gesche Berkhan5Frank Hahn6Zentrum für Biomolekulare Wirkstoffe, Leibniz-Universität Hannover, Schneiderberg 38, 30167 Hannover, GermanyZentrum für Biomolekulare Wirkstoffe, Leibniz-Universität Hannover, Schneiderberg 38, 30167 Hannover, GermanyProfessur für Organische Chemie (Lebensmittelchemie), Fakultät für Biologie, Chemie und Geowissenschaften, Universitätsstraße 30, 95447 Bayreuth, GermanyZentrum für Biomolekulare Wirkstoffe, Leibniz-Universität Hannover, Schneiderberg 38, 30167 Hannover, GermanyProfessur für Organische Chemie (Lebensmittelchemie), Fakultät für Biologie, Chemie und Geowissenschaften, Universitätsstraße 30, 95447 Bayreuth, GermanyZentrum für Biomolekulare Wirkstoffe, Leibniz-Universität Hannover, Schneiderberg 38, 30167 Hannover, GermanyZentrum für Biomolekulare Wirkstoffe, Leibniz-Universität Hannover, Schneiderberg 38, 30167 Hannover, GermanyWe describe the characterisation of the O-methyltransferase JerF from the late stages of jerangolid biosynthesis. JerF is the first known example of an enzyme that catalyses the formation of a non-aromatic, cyclic methylenolether. The enzyme was overexpressed in E. coli and the cell-free extracts were used in bioconversion experiments. Chemical synthesis gave access to a series of substrate surrogates that covered a broad structural space. Enzymatic assays revealed a broad substrate tolerance and high regioselectivity of JerF, which makes it an attractive candidate for an application in chemoenzymatic synthesis with particular usefulness for late stage application on 4-methoxy-5,6-dihydro-2H-pyran-2-one-containing natural products.http://www.mdpi.com/1420-3049/21/11/1443methyltransferasesenzymeschemoenzymatic synthesisnatural productschemoselectivitymethylenolethers |
| spellingShingle | Steffen Friedrich Franziska Hemmerling Frederick Lindner Anna Warnke Johannes Wunderlich Gesche Berkhan Frank Hahn Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis Molecules methyltransferases enzymes chemoenzymatic synthesis natural products chemoselectivity methylenolethers |
| title | Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis |
| title_full | Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis |
| title_fullStr | Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis |
| title_full_unstemmed | Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis |
| title_short | Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis |
| title_sort | characterisation of the broadly specific o methyl transferase jerf from the late stages of jerangolid biosynthesis |
| topic | methyltransferases enzymes chemoenzymatic synthesis natural products chemoselectivity methylenolethers |
| url | http://www.mdpi.com/1420-3049/21/11/1443 |
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