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| Hauptseite > Publikationsdatenbank > One-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants > print |
| Hauptseite > Publikationsdatenbank > One-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants > print |
| 001 | 823900 | ||
| 005 | 20210129224902.0 | ||
| 024 | 7 | _ | |a 10.1002/cctc.201600973 |2 doi |
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| 100 | 1 | _ | |a Le-Huu, Priska |0 P:(DE-HGF)0 |b 0 |
| 245 | _ | _ | |a One-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants |
| 260 | _ | _ | |a Weinheim |c 2016 |b WILEY-VCH Verlag |
| 336 | 7 | _ | |a article |2 DRIVER |
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| 520 | _ | _ | |a Cytochrome P450 monooxygenases (P450s) are involved in the biosynthesis of a wide range of bioactive secondary metabolites. They often introduce several oxy functionalities at different positions of a substrate through multiple steps and produce a range of oxidized derivatives. Herein, we describe a one-pot two-step hydroxylation of the diterpenoid b-cembrenediol isolated from the plant Nicotiana tabacum. This 14-membered macrocycle shows neuroprotective effects and is, along with its oxidized derivatives, of pharmaceutical interest. Sequential hydroxylations catalyzed by the regioselective P450 BM3 mutants F87A/I263L and V78A/F87G yielded the epimeric (9S,10R/S)-b-cembrenetetraols with a diastereomeric ratio of 48:52. The replacement of the mutant V78A/F87G with L75A/ V78A/F87G in the second step improves the diastereomeric ratio up to 10:90. Absolute configurations of the newly introduced hydroxy groups were determined by quantum-mechanical calculations of NMR spectra. |
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| 773 | _ | _ | |a 10.1002/cctc.201600973 |0 PERI:(DE-600)2501161-3 |n 24 |p 3755-3761 |t ChemCatChem |v 8 |y 2016 |x 1867-3880 |
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