Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 22, Issue 20, Pages 5687-5691Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2014.05.046
Keywords
Light-driven P450 BM3 biocatalyst; Stereoselective hydroxylation; Allylic oxidation; (R)-9-Hydroxy-10-undecenoic acid; Natural product synthesis
Funding
- National Institute of Health [GM095415]
- Research Corporation for Science Advancement
- National Science Foundation (MRI) [0923573]
- Direct For Biological Sciences
- Div Of Biological Infrastructure [0923573] Funding Source: National Science Foundation
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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. (C) 2014 Elsevier Ltd. All rights reserved.
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