Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida
Toluene dioxygenase, a multicomponent enzyme system known to oxidize mononuclear aromatic hydrocarbons to cis-dihydrodiols, oxidized indene and indan to 1-indenol and 1-indanol, respectively. In addition, the enzyme catalyzed dioxygen addition to the nonaromatic double bond of indene to form cis-1,2-indandiol. The oxygen atoms in 1-indenol and cis-1,2-indandiol were shown to be derived from molecular oxygen, whereas 70% of the oxygen in 1-indanol was derived from water. All of the isolated products were optically active as demonstrated by /sup 19/F NMR and HPLC discrimination of diastereomeric esters and by chiroptic methods. The high optical purity of (-)-(1R)-indanol (84% enantiomeric excess) and the failure of scavengers of reactive oxygen species to inhibit the monooxygenation reaction supported the contention that monooxygen insertion is mediated by an active-site process. Experiments with 3-(/sup 2/H) indene indicated that equilibration between C-1 and C-3 occurred prior to the formation of the carbon-oxygen bond to yield 1-indenol. Naphthalene dioxygenase also oxidized indan to 1-indanol, which suggested that benzylic monoxygenation may be typical of this group of dioxygenases.
- Research Organization:
- Univ. of Texas, Austin (USA)
- OSTI ID:
- 5410589
- Journal Information:
- Biochemistry; (United States), Vol. 27:4
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
62 RADIOLOGY AND NUCLEAR MEDICINE
INDAN
OXIDATION
INDENE
OXYGENASES
NUCLEAR MAGNETIC RESONANCE
AROMATICS
FLUORINE 19
GLYCOLS
HYDROCARBONS
LIQUID COLUMN CHROMATOGRAPHY
PROTONS
PSEUDOMONAS
STEREOCHEMISTRY
TOLUENE
ALCOHOLS
ALKYLATED AROMATICS
BACTERIA
BARYONS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CONDENSED AROMATICS
ELEMENTARY PARTICLES
ENZYMES
FERMIONS
FLUORINE ISOTOPES
HADRONS
HYDROXY COMPOUNDS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MICROORGANISMS
NUCLEI
NUCLEONS
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
OXIDOREDUCTASES
RESONANCE
SEPARATION PROCESSES
STABLE ISOTOPES
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