Thiol-mediated oxidation of nonphenolic lignin model compounds by manganese peroxidase of Phanerochaete chrysosporium
- Oregon Graduate Center, Beaverton (United States)
In the presence of Mn{sup II}, H{sub 2}O{sub 2}, and glutathione (GSH), manganese peroxidase oxidized veratryl alcohol (1) to veratraldehyde (4). Anisyl alcohol (2) and benzyl alcohol (3) were also oxidized by this system to their corresponding aldehydes, anisaldehyde (5) and benzaldehyde (6). In the presence of GSH, chemically prepared Mn{sup III} or {gamma}-irradiation also catalyzed the oxidation of 1, 2, and 3 to 4, 5, and 6, respectively. GSH and dithiothreitol rapidly reduced Mn{sup III} to Mn{sup II} in the absence of aromatic substrates and the dithiothreitol was oxidized to its disulfide (4,5-dihydroxyl-1,2-dithiane). These results indicate that the thiol is oxidized by enzyme-generated Mn{sup III} to a thiyl radical. The latter abstracts a hydrogen from the substrate , forming a benzylic radical which reacts with another thiyl radical to yield an intermediate which decomposes to the benzaldehyde product. 51 refs., 5 figs., 2 tabs.
- DOE Contract Number:
- FG06-86ER13550
- OSTI ID:
- 5917143
- Journal Information:
- Journal of Biological Chemistry; (United States), Vol. 264:24; ISSN 0021-9258
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
LIGNIN
OXIDATION
PHANEROCHAETE
ENZYME ACTIVITY
ABSORPTION SPECTROSCOPY
AEROBIC CONDITIONS
ALCOHOLS
ALDEHYDES
ANAEROBIC CONDITIONS
CHARGE STATES
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
EXPERIMENTAL DATA
GAMMA RADIATION
GLUTATHIONE
HYDROGEN PEROXIDE
MANGANESE COMPLEXES
MASS SPECTROSCOPY
PEROXIDASES
PH VALUE
RADIATION CHEMISTRY
RADICALS
REACTION INTERMEDIATES
THIOLS
THIYL RADICALS
ULTRAVIOLET SPECTRA
VISIBLE SPECTRA
CARBOHYDRATES
CHEMISTRY
COMPLEXES
DATA
DRUGS
ELECTROMAGNETIC RADIATION
ENZYMES
EUMYCOTA
FUNGI
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFORMATION
IONIZING RADIATIONS
KINETICS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDOREDUCTASES
OXYGEN COMPOUNDS
PEPTIDES
PEROXIDES
PLANTS
POLYPEPTIDES
POLYSACCHARIDES
PROTEINS
RADIATIONS
RADIOPROTECTIVE SUBSTANCES
REACTION KINETICS
SACCHARIDES
SPECTRA
SPECTROSCOPY
SYNTHESIS
TRANSITION ELEMENT COMPLEXES
090900* - Biomass Fuels- Processing- (1990-)
550700 - Microbiology