title: Bioconversion of substituted naphthalenes and β-eudesmol with the cytochrome P450 BM3 variant F87V.
abstract: Bioconversion of various substituted naphthalenes that contain 1-methoxy- and 1-ethoxy-naphthalenes, methylnaphthalenes, dimethylnaphthalenes, and naphthalenecarboxylic acid methyl esters were performed using recombinant Escherichia coli cells, which expressed the gene coding for a cytochrome P450 BM3 variant F87V (P450 BM3 (F87V)) that was N-terminally fused to an archaeal peptidyl-prolyl cis-trans isomerase. In addition, bioconversion experiments with the same substrates were carried out using those that expressed the phnA1A2A3A4 genes for a polycyclic aromatic hydrocarbon (PAH)-dihydroxylating dioxygenase, which originated from a PAH-utilizing marine bacterium Cycloclasticus sp. strain A5. Consequently, a variety of mono-hydroxylated derivatives were generated from these substituted naphthalenes. Oxidative aryl coupling was found to produce a novel compound 4,4'-diethoxy-[2,2']-binaphthalenyl-1,1'-diol from 1-ethoxynaphthalene with the E. coli cells expressing the P450 BM3 (F87V) gene. This recombinant E. coli was further shown to introduce the hydroxyl group regio- and stereo-specifically into a sesquiterpene β-eudesmol.
authors.affiliation: Marine Biotechnology Institute, Heita, Kamaishi, Iwate, 026-0001, Japan. n-misawa@ishikawa-pu.ac.jp
authors.forename: Norihiko
authors.initials: N
authors.lastname: Misawa
authors.forename: Miho
authors.initials: M
authors.lastname: Nodate
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Otomatsu
authors.forename: Keiko
authors.initials: K
authors.lastname: Shimizu
authors.forename: Chie
authors.initials: C
authors.lastname: Kaido
authors.forename: Miho
authors.initials: M
authors.lastname: Kikuta
authors.forename: Akira
authors.initials: A
authors.lastname: Ideno
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Ikenaga
authors.forename: Jun
authors.initials: J
authors.lastname: Ogawa
authors.forename: Sakayu
authors.initials: S
authors.lastname: Shimizu
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Shindo
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry / Q000235:genetics* / Q000378:metabolism*; D001711:Biotransformation; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000235:genetics* / Q000378:metabolism*; D014644:Genetic Variation; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism*; D044147:Piscirickettsiaceae / Q000201:enzymology*; D015202:Protein Engineering; D045787:Sesquiterpenes, Eudesmane / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D001426:Bacterial Proteins; D009281:Naphthalenes; D045787:Sesquiterpenes, Eudesmane; C051082:beta-eudesmol; D003577:Cytochrome P-450 Enzyme System