title: Product Rearrangement from Altering a Single Residue in the Rice syn-Copalyl Diphosphate Synthase.
abstract: Through site-directed mutagenesis targeted at identification of the catalytic base in the rice (Oryza sativa) syn-copalyl diphosphate synthase OsCPS4, changes to a single residue (H501) were found to induce rearrangement rather than immediate deprotonation of the initially formed bicycle, leading to production of the novel compound syn-halimadienyl diphosphate. These mutational results are combined with quantum chemical calculations to provide insight into the underlying reaction mechanism.
authors.affiliation: Roy J. Carver Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University , Ames, Iowa 50011, United States.
authors.forename: Kevin C
authors.initials: KC
authors.lastname: Potter
authors.affiliation: Roy J. Carver Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University , Ames, Iowa 50011, United States.
authors.forename: Meirong
authors.initials: M
authors.lastname: Jia
authors.affiliation: Department of Chemistry, University of California , Davis, California 95616, United States.
authors.forename: Young J
authors.initials: YJ
authors.lastname: Hong
authors.affiliation: Department of Chemistry, University of California , Davis, California 95616, United States.
authors.forename: Dean
authors.initials: D
authors.lastname: Tantillo
authors.affiliation: Roy J. Carver Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University , Ames, Iowa 50011, United States.
authors.forename: Reuben J
authors.initials: RJ
authors.lastname: Peters
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000378:metabolism*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification; D051231:Farnesyltranstransferase / Q000378:metabolism; D015394:Molecular Structure; D012275:Oryza / Q000201:enzymology* / Q000235:genetics; D010940:Plant Proteins / Q000378:metabolism*; D020950:Vitex / Q000737:chemistry
chemical_list: D004224:Diterpenes; D010940:Plant Proteins; D019883:Alkyl and Aryl Transferases; C090963:ent-kaurene synthetase A; D051231:Farnesyltranstransferase