Microsomal hydroxylation of specifically deuterated monosubstituted benzenes. Evidence for direct aromatic hydroxylation

Journal Article · Tue Jun 19 04:00:00 EDT 1984 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00308a031· OSTI ID:5554045

Hanzlik, R P; Hogberg, K; Judson, C M

The aromatic hydroxylation of six pairs of selectively deuterated monosubstituted benzenes was investigated with rat liver microsomes of various induction states. The substrates studied included 3,5-D/sub 2/C/sub 6/H/sub 3/X and 2,4,6-D/sub 3/C/sub 6/H/sub 2/X, where X = Br, CN, NO/sub 2/, OCH/sub 3/, CH/sub 3/, or Ph, respectively. The deuterium content of the ortho, meta, and para hydroxylated metabolites, as well as side chain oxidation products was determined by capillary gas chromatography-mass spectroscopy. These data were analyzed according to a hypothetical model in which a molecule of substrate can undergo either direct aromatic hydroxylation (defined as obligatory and complete loss of deuterium from the site of hydroxylation) or indirect aromatic hydroxylation (defined as the obligatory and complete shift of deuterium to an adjacent position, followed by its partial loss as governed by a kinetic deuterium isotope effect).

• Research Organization: Univ. of Kansas, Lawrence
• OSTI ID: 5554045
• Journal Information: Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 23:13; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

560301* -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANIMALS
AROMATICS
BENZENE
BIOCHEMICAL REACTION KINETICS
BIOLOGICAL PATHWAYS
BODY
CELL CONSTITUENTS
CHROMATOGRAPHY
DATA
DATA ANALYSIS
DEUTERIUM
DIGESTIVE SYSTEM
EXPERIMENTAL DATA
GAS CHROMATOGRAPHY
GLANDS
HYDROCARBONS
HYDROGEN ISOTOPES
HYDROXYLATION
INFORMATION
ISOTOPE EFFECTS
ISOTOPES
KINETICS
LIGHT NUCLEI
LIVER
MAMMALS
MASS SPECTROSCOPY
MATHEMATICAL MODELS
METABOLISM
METABOLITES
MICROSOMES
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANOIDS
ORGANS
RATS
REACTION KINETICS
RODENTS
SEPARATION PROCESSES
SPECTROSCOPY
STABLE ISOTOPES
VERTEBRATES