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Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis |
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| Affiliation: | 1. Department of Pharmaceutical and Biomedical Sciences, University of Georgia, 240 W. Green St., Athens, GA 30602, USA;2. Department of Medicinal Chemistry, University of Washington, HSB H-172, Seattle, WA 98195, USA;3. Department of Biological Structure and Biochemistry, University of Washington, HSB G520, Seattle, WA 98195-7420, USA;4. Department of Biochemistry, University of Washington, HSB J405, Seattle, WA 98195-7350, USA;5. Department of Pharmaceutical Sciences, University of Colorado Denver, Anschutz Medical Campus, Box C238-P15, Aurora, CO 80045, USA |
| Abstract: | We report herein the selective hydroxylation of 10-undecenoic acid with a light-activated hybrid P450 BM3 enzyme. Under previously developed photocatalytic reaction conditions, only a monohydroxylated product is detected by gas chromatography. Hydroxylation occurs exclusively at the allylic position as confirmed from a synthesized authentic standard. Investigation into the stereochemistry of the reaction indicates that the R enantiomer is obtained in 85% ee. The (R)-9-hydroxy-10-undecenoic acid obtained enzymatically is a valuable synthon en route to various natural products further expanding the light-activated P450 BM3 biocatalysis and highlighting the advantages over traditional methods. |
| Keywords: | Light-driven P450 BM3 biocatalyst Stereoselective hydroxylation Allylic oxidation Natural product synthesis |
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