title: Discrimination of the prochiral hydrogens at the C-2 position of n-alkanes by the methane/ammonia monooxygenase family proteins.
abstract: The selectivity of ammonia monooxygenase from Nitrosomonas europaea (AMO-Ne) for the oxidation of C4-C8n-alkanes to the corresponding alcohol isomers was examined to show the ability of AMO-Ne to recognize the n-alkane orientation within the catalytic site. AMO-Ne in whole cells produces 1- and 2-alcohols from C4-C8n-alkanes, and the regioselectivity is dependent on the length of the carbon chain. 2-Alcohols produced from C4-C7n-alkanes were predominantly either the R- or S-enantiomers, while 2-octanol produced from n-octane was racemic. These results indicate that AMO-Ne can discriminate between the prochiral hydrogens at the C-2 position, with the degree of discrimination varying according to the n-alkane. Compared to the particulate methane monooxygenase (pMMO) of Methylococcus capsulatus (Bath) and that of Methylosinus trichosporium OB3b, AMO-Ne showed a distinct ability to discriminate between the orientation of n-butane and n-pentane in the catalytic site.
authors.affiliation: Department of Environmental Chemistry and Engineering, Tokyo Institute of Technology, 4259 G-1-14 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan. tbaba@chemenv.titech.ac.jp.
authors.forename: Akimitsu
authors.initials: A
authors.lastname: Miyaji
authors.forename: Teppei
authors.initials: T
authors.lastname: Miyoshi
authors.forename: Ken
authors.initials: K
authors.lastname: Motokura
authors.forename: Toshihide
authors.initials: T
authors.lastname: Baba
mesh_terms: D000473:Alkanes / Q000378:metabolism*; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000378:metabolism; D001665:Binding Sites; D002073:Butanes / Q000378:metabolism; D000440:Butanols / Q000378:metabolism; D004583:Electrons; D006859:Hydrogen / Q000378:metabolism*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009606:Nitrosomonas / Q000201:enzymology; D010088:Oxidoreductases / Q000378:metabolism*; D010105:Oxygenases / Q000737:chemistry / Q000378:metabolism*; D010420:Pentanes / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000473:Alkanes; D000596:Amino Acids; D002073:Butanes; D000440:Butanols; D010420:Pentanes; C033353:pentane; C046888:butane; D006859:Hydrogen; D010088:Oxidoreductases; D010105:Oxygenases; C021555:methane monooxygenase; C045582:ammonia monooxygenase