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• W2831266945 abstract "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)." @default.
• W2831266945 created "2018-07-19" @default.
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• W2831266945 date "2018-07-06" @default.
• W2831266945 modified "2023-10-12" @default.
• W2831266945 title "Chemoenzymatic Synthesis of the Intermediates in the Peppermint Monoterpenoid Biosynthetic Pathway" @default.
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• W2831266945 doi "https://doi.org/10.1021/acs.jnatprod.7b01026" @default.
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