Oxidation of Acetaminophen

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acetaminophen

Summary of ESR Data

Summary of Hyperfine Coupling
Nucle (# of spins) hyperfine hyperfine hyperfine
Ref --> West, 1984 Fischer, 1986 Sturgeon, not published
Conditions fast-flow, pH 7.5 fast-flow, pH 7.5 immoblized-Enzyme, pH 5/dioxane (50/50)
Spectrum unresolved triplet high res multiline med res multiline
N (1) nr 0.81 G 1.68 G
H, on nitrogen (1) nr 1.35 G 0.96 G
H, ortho (2) 5.2 G 5.11 G 5.19 G
H, meta (2) nr 0.64 G 0.76 G
H, methyl (3) nr 1.01 G nr

nr = not reported or not resolved

HRP/H2O2

West 1984, Fischer,1985
Fischer 1986
Sturgeon, unpublished
ACETAMINOPHEN - ENZYMATIC FORMATION OF A TRANSIENT PHENOXYL FREE-RADICAL
West, PR, Harman, LS, Josephy, PD, Mason, RP
Biochemical pharmacology, 1984, Vol.33(18), pp.2933-2936.
Free-Radical Metabolites of Acetaminophen and a Dimethylated Derivative
Volker Fischer, Paul R. West, Laura S. Harman, and Ronald P. Mason.
Environmental Health Perspectives, 1985, 64, pp. 127-137.
Direct electron spin resonance detection of free radical intermediates during the peroxidase catalyzed oxidation of phenacetin metabolites.
Volker Fischer, Laura S. Harman, Paul R. West, and Ronald P. Mason.
Chem.-Biol. Interactions, 1986, Vol 60, PP. 115-127.

HRP/H2O2/Acetaminophen analog

Stable Free Radical and Benzoquinone Imine Metabolites of an Acetaminophen Analogue
Volker Fischer and Ronald P. Mason.
Journal of Biological Chemistry, 1984, 259(16), pp. 10284-10288.
here
Fischer, 1984
Fischer, 1984

with GSH

Media:J. Biol. Chem.-1990-Ramakrishna Rao-844-7.pdf

Oxidation Product Analysis

Identification of Acetaminophen Polymerization Products Catalyzed by Horseradish Peroxidase.
David W. Potter$, Dwight W. Miller, and Jack A. Hinson
Journal of Biological Chemistry, 1985 "260(22), pp 12174-12180.
here
Fischer, 1984

Related Phenacetin

http://www.ncbi.nlm.nih.gov/pubmed/3024853