The stereochemical course of 2-methylisoborneol biosynthesis
Both enantiomers of 2-methyllinalyl diphosphate (2-Me-LPP) were synthesized enantioselectively using Sharpless epoxidation as a key step and purification of enantiomerically enriched intermediates through HPLC separation on a chiral stationary phase. Their enzymatic conversion with 2-methylisoborneo...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.82 |
| _version_ | 1818010687982534656 |
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| author | Binbin Gu Anwei Hou Jeroen S. Dickschat |
| author_facet | Binbin Gu Anwei Hou Jeroen S. Dickschat |
| author_sort | Binbin Gu |
| collection | DOAJ |
| description | Both enantiomers of 2-methyllinalyl diphosphate (2-Me-LPP) were synthesized enantioselectively using Sharpless epoxidation as a key step and purification of enantiomerically enriched intermediates through HPLC separation on a chiral stationary phase. Their enzymatic conversion with 2-methylisoborneol synthase (2MIBS) demonstrates that (R)-2-Me-LPP is the on-pathway intermediate, while a minor formation of 2-methylisoborneol from (S)-2-Me-LPP may be explained by isomerization to 2-Me-GPP and then to (R)-2-Me-LPP. |
| first_indexed | 2024-04-14T05:58:41Z |
| format | Article |
| id | doaj.art-3db49b027d0c4ea2af3caaadd38ad04b |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-14T05:58:41Z |
| publishDate | 2022-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-3db49b027d0c4ea2af3caaadd38ad04b2022-12-22T02:08:51ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-07-0118181882410.3762/bjoc.18.821860-5397-18-82The stereochemical course of 2-methylisoborneol biosynthesisBinbin Gu0Anwei Hou1Jeroen S. Dickschat2Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany Both enantiomers of 2-methyllinalyl diphosphate (2-Me-LPP) were synthesized enantioselectively using Sharpless epoxidation as a key step and purification of enantiomerically enriched intermediates through HPLC separation on a chiral stationary phase. Their enzymatic conversion with 2-methylisoborneol synthase (2MIBS) demonstrates that (R)-2-Me-LPP is the on-pathway intermediate, while a minor formation of 2-methylisoborneol from (S)-2-Me-LPP may be explained by isomerization to 2-Me-GPP and then to (R)-2-Me-LPP.https://doi.org/10.3762/bjoc.18.82biosynthesisenantioselective synthesisenzyme mechanismsgas chromatographyterpenoids |
| spellingShingle | Binbin Gu Anwei Hou Jeroen S. Dickschat The stereochemical course of 2-methylisoborneol biosynthesis Beilstein Journal of Organic Chemistry biosynthesis enantioselective synthesis enzyme mechanisms gas chromatography terpenoids |
| title | The stereochemical course of 2-methylisoborneol biosynthesis |
| title_full | The stereochemical course of 2-methylisoborneol biosynthesis |
| title_fullStr | The stereochemical course of 2-methylisoborneol biosynthesis |
| title_full_unstemmed | The stereochemical course of 2-methylisoborneol biosynthesis |
| title_short | The stereochemical course of 2-methylisoborneol biosynthesis |
| title_sort | stereochemical course of 2 methylisoborneol biosynthesis |
| topic | biosynthesis enantioselective synthesis enzyme mechanisms gas chromatography terpenoids |
| url | https://doi.org/10.3762/bjoc.18.82 |
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