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Enzymatic O-Methylation of Epinephrine and Other Catechols
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“The O-methylation of catechols plays an important role in the phase 2 metabolism of estrogens (Section 4.4.1) and is catalyzed by the enzyme catechol-O-methyltransferase (COMT) [179]”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [179]
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“(4) No difference in the expression of hydroxyls of a catechol, leading to catecholamine inactivation (Axelrod and Tomchick, 1958).”
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“Such a function may not be needed for stronger Lewis acids of comparable ionic radius such as Mn2+, Co2+, Zn2+ and Fe2+, which can functionally replace Mg2+ (Axelrod & Tomchick, 1958).”
BackgroundThe V108M mutation decreases the structural stability of catechol O-methyltransferase
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The Val158Met polymorphism in COMT gene and cancer risk: role of endogenous and exogenous catechols
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“This enzyme was first described and characterized by Dr. Julius Axelrod and his coworkers in the soluble fraction of liver and other organ tissues already in 1958 (Axelrod et al., 1958; Axelrod & Tomchichk, 1958).”
MethodAdolescence is the starting point of sex-dichotomous COMT genetic effects
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Catechol-O-Methyltransferase Val158Met Polymorphism and Antisaccade Eye Movements in Schizophrenia
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“ine to a hydroxyl group located on a catechol nucleus [1].”
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“Catechol-O-methyltransferase (COMT) catalyzes the methylation of catechol structures, including dopamine, norepinephrine, epinephrine, caffeine and catechol estrogens (Axelrod and Tomchick, 1958).”
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“Catechol-O-methyltransferase (COMT) catalyzes the transfer of a methyl group from S-adenosylmethionine to catecholamines, including the neurotransmitters dopamine, epinephrine, and norepinephrine.(45) A variant caused by a G-to-A transition at codon 158 of the COMT gene results in a valine-to-methionine substitution.”
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“3), include L-dopa, epinephrine, norepinephrine, dopamine; their hydroxylated metabolites like 3,4dihydroxymandelic acid, 3,4-dihydroxyphenylacetic acid, 3,4-dihydroxybenzoic acid, 3,4-dihydroxyphenylethanol, 3,4-dihydroxyphenylglycol, N-acetyldopamine, Nacetylnoradrenaline [26], catechol estrogens (2-hydroxyestradiol…”
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“The catechol-O-methyltransferase was obtained from rat livers by the purification procedure of Axelrod and Tomchick (1).”
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Directed O methylation of estrogen catechol sulfates
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THE BIOGENESIS OF CONJUGATION AND DETOXICATION PRODUCTS
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“efficiency [33–35] and the gene (DBH) coding for dopamine beta hydroxylase (dopamine metabolization enzyme) Table 1 [16].”
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Metadata
- Authors
- Axelrod, J., & Tomchick, R.
- Affiliations
- United States Public Health Service (US)
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1958-09
- Volume
- 233
- Issue
- 3
- Pages
- 702-705
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1543624067
- Cited by
- 1,283
- References
- 16
- Citations by year
- 2026: 6 · 2025: 8 · 2024: 8 · 2023: 12 · 2022: 14 · 2021: 19 · 2020: 11 · 2019: 16 · 2018: 13 · 2017: 15 · 2016: 28 · 2015: 12 · 2014: 14 · 2013: 19 · 2012: 21
- FWCI
- 55.85
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Microbial metabolism and enzyme function
- Keywords
- epinephrine, catechol, O-methylation, enzymatic methylation, catecholamine metabolism
- MeSH terms
- Catechols, Epinephrine, Methylation, Norepinephrine, Transferases
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