Difference between revisions of "Oxidation of Acetaminophen"
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| + | [[File:Acetaminophen.png|200px|thumb|center|acetaminophen]] | ||
| + | ==Summary of ESR Data== | ||
| + | {| border=1 | ||
| + | |+Summary of Hyperfine Coupling | ||
| + | |-bgcolor=gray | ||
| + | !Nucle (# of spins)!!hyperfine!!hyperfine!!hyperfine | ||
| + | |- | ||
| + | |Ref --> ||align=center|West, 1984||align=center|Fischer, 1986||align=center|Sturgeon, not published | ||
| + | |- | ||
| + | |Conditions ||align=center|fast-flow, pH 7.5||align=center|fast-flow, pH 7.5||align=center|immoblized-Enzyme, pH 5/dioxane (50/50) | ||
| + | |- | ||
| + | |Spectrum ||unresolved triplet||high res multiline||med res multiline | ||
| + | |- | ||
| + | | N (1) || align=center|nr|| align=center|0.81 G ||align=center|1.68 G | ||
| + | |- | ||
| + | | H, on nitrogen (1) || align=center|nr || align=center|1.35 G ||align=center|0.96 G | ||
| + | |- | ||
| + | | H, ortho (2) || align=center|5.2 G|| align=center|5.11 G || align=center|5.19 G | ||
| + | |- | ||
| + | | H, meta (2) ||align=center| nr || align=center|0.64 G|| align=center|0.76 G | ||
| + | |- | ||
| + | | H, methyl (3) ||align=center|nr || align=center|1.01 G ||align=center|nr | ||
| + | |} | ||
| + | |||
| + | nr = not reported or not resolved | ||
| + | |||
==HRP/H2O2== | ==HRP/H2O2== | ||
| − | + | {| | |
| − | : | + | |[[File:APAP rad HRP.png|200px|thumb|center|West 1984, Fischer,1985]] |
| − | + | ||[[File:Screen Shot 2018-07-15 at 7.38.54 AM.png|230px|thumb|center|Fischer 1986]] | |
| − | + | ||[[File:WIU FigX.jpg|230px|thumb|center|Sturgeon, unpublished]] | |
| − | [[File: | ||
| + | |} | ||
| + | :'''ACETAMINOPHEN - ENZYMATIC FORMATION OF A TRANSIENT PHENOXYL FREE-RADICAL''' | ||
| + | :West, PR, Harman, LS, Josephy, PD, Mason, RP | ||
| + | :[[Media:West 1984.pdf|''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. | ||
| + | :[[Media:Envhper00447-0129.pdf|''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. | ||
| + | :[[Media:APAP radical mason.pdf|''Chem.-Biol. Interactions'', '''1986''', ''Vol 60'', PP. 115-127.]] | ||
| − | :[[Media:J. Biol. Chem.-1984-Fischer-10284-8.pdf]] | + | ==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. | ||
| + | :[[Media:J. Biol. Chem.-1984-Fischer-10284-8.pdf|here]] | ||
| + | [[File:DM APAP oxidation.png|400px|thumb|center|Fischer, 1984]] | ||
| + | [[File:DMA rad HRP.png|200px|thumb|center|Fischer, 1984]] | ||
| − | + | ==with GSH== | |
:[[Media:J. Biol. Chem.-1990-Ramakrishna Rao-844-7.pdf]] | :[[Media:J. Biol. Chem.-1990-Ramakrishna Rao-844-7.pdf]] | ||
| − | Oxidation Product Analysis | + | ==Oxidation Product Analysis== |
| − | :[[Media:J. Biol. Chem.-1985-Potter-12174-80.pdf]] | + | :'''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. | ||
| + | :[[Media:J. Biol. Chem.-1985-Potter-12174-80.pdf|here]] | ||
| + | [[File:APAP Ox products.png|200px|thumb|center|Fischer, 1984]] | ||
| + | |||
| + | ==Related Phenacetin== | ||
| + | http://www.ncbi.nlm.nih.gov/pubmed/3024853 | ||
Latest revision as of 01:00, 16 July 2018
Summary of ESR Data
| 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
- 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
with GSH
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
