| Autor: |
Aisling Ní, Cheallaigh, David J, Mansell, Helen S, Toogood, Shirley, Tait, Antonios, Lygidakis, Nigel S, Scrutton, John M, Gardiner |
| Rok vydání: |
2018 |
| Předmět: |
|
| Zdroj: |
Journal of natural products. 81(7) |
| ISSN: |
1520-6025 |
| Popis: |
A chemoenzymatic approach providing access to all four intermediates in the peppermint biosynthetic pathway between limonene and menthone/isomenthone, including noncommercially available intermediates (-)- trans-isopiperitenol (2), (-)-isopiperitenone (3), and (+)- cis-isopulegone (4), is described. Oxidation of (+)-isopulegol (13) followed by enolate selenation and oxidative elimination steps provides (-)-isopiperitenone (3). A chemical reduction and separation route from (3) provides both native (-)- trans-isopiperitenol (2) and isomer (-)- cis-isopiperitenol (18), while enzymatic conjugate reduction of (-)-isopiperitenone (3) with IPR [(-)-isopiperitenone reductase)] provides (+)- cis-isopulegone (4). This undergoes facile base-mediated chemical epimerization to (+)-pulegone (5), which is subsequently shown to be a substrate for NtDBR ( Nicotiana tabacum double-bond reductase) to afford (-)-menthone (7) and (+)-isomenthone (8). |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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