title: Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis.
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.
authors.affiliation: San Jose State University, One Washington Square, San José, CA 95192-0101, United States.
authors.forename: Mallory
authors.initials: M
authors.lastname: Kato
authors.affiliation: San Jose State University, One Washington Square, San José, CA 95192-0101, United States.
authors.forename: Daniel
authors.initials: D
authors.lastname: Nguyen
authors.affiliation: San Jose State University, One Washington Square, San José, CA 95192-0101, United States.
authors.forename: Melissa
authors.initials: M
authors.lastname: Gonzalez
authors.affiliation: San Jose State University, One Washington Square, San José, CA 95192-0101, United States.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Cortez
authors.affiliation: San Jose State University, One Washington Square, San José, CA 95192-0101, United States.
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Mullen
authors.affiliation: San Jose State University, One Washington Square, San José, CA 95192-0101, United States. Electronic address: lionel.cheruzel@sjsu.edu.
authors.forename: Lionel E
authors.initials: LE
authors.lastname: Cheruzel
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D055162:Biocatalysis; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism*; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D006900:Hydroxylation; D008027:Light; D008958:Models, Molecular; D015394:Molecular Structure; D009251:NADPH-Ferrihemoprotein Reductase / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D013237:Stereoisomerism; D014476:Undecylenic Acids / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001426:Bacterial Proteins; D001688:Biological Products; D014476:Undecylenic Acids; D003577:Cytochrome P-450 Enzyme System; D009251:NADPH-Ferrihemoprotein Reductase; C052423:flavocytochrome P450 BM3 monoxygenases; C538763:undecylenic acid
keywords: (R)-9-Hydroxy-10-undecenoic acid; Allylic oxidation; Light-driven P450 BM3 biocatalyst; Natural product synthesis; Stereoselective hydroxylation