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000823900 1001_ $$0P:(DE-HGF)0$$aLe-Huu, Priska$$b0
000823900 245__ $$aOne-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants
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000823900 520__ $$aCytochrome P450 monooxygenases (P450s) are involved in the biosynthesis of a wide range of bioactive secondary metabolites. They often introduce several oxy functionalities at different positions of a substrate through multiple steps and produce a range of oxidized derivatives. Herein, we describe a one-pot two-step hydroxylation of the diterpenoid b-cembrenediol isolated from the plant Nicotiana tabacum. This 14-membered macrocycle shows neuroprotective effects and is, along with its oxidized derivatives, of pharmaceutical interest. Sequential hydroxylations catalyzed by the regioselective P450 BM3 mutants F87A/I263L and V78A/F87G yielded the epimeric (9S,10R/S)-b-cembrenetetraols with a diastereomeric ratio of 48:52. The replacement of the mutant V78A/F87G with L75A/ V78A/F87G in the second step improves the diastereomeric ratio up to 10:90. Absolute configurations of the newly introduced hydroxy groups were determined by quantum-mechanical calculations of NMR spectra.
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000823900 7001_ $$0P:(DE-Juel1)165744$$aPetrović, Dušan$$b1$$ufzj
000823900 7001_ $$0P:(DE-Juel1)132024$$aStrodel, Birgit$$b2$$ufzj
000823900 7001_ $$0P:(DE-HGF)0$$aUrlacher, Vlada B.$$b3$$eCorresponding author
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