The DOI matches its Crossref record; 45 of the 50 references it cites were found in a registry or an index.
Mechanistic studies on aromatase and related CC bond cleaving P-450 enzymes
Abstract
Some P-450 systems, notably aromatase and 14 alpha-demethylase catalyse not only the hydroxylate reaction but also the oxidation of an alcohol into a carbonyl compound as well as a C-C bond cleavage process. All these reactions occur at the same active site. A somewhat analogous situation is noted with 17 alpha-hydroxylase-17,20-lyase that participates in hydroxylation as well as C-C bond cleavage process. The C-C bond cleavage reactions catalysed by the above enzymes conform to the general equation: [formula: see text] It is argued that all three types of reaction catalyzed by these enzymes may be viewed as variations on a common theme. In P-450 dependent hydroxylation the initially formed FeIII-O-O. species is converted into FeIII-O-OH and the heterolysis of the oxygen-oxygen bond of the latter then gives the oxo-derivative for which a number of canonical structures are possible; for example FeV = O<==>(+.)FeIV = O<==>FeIV-O.. One of these, FeIV-O. behaves like an alkoxyl radical and participates in hydrogen abstraction from C-H bond to produce FeIV-OH and carbon radical. The latter is then quenched by the delivery of hydroxyl radical from FeIV-OH. The latter species may thus be regarded as a carrier of hydroxyl radical. We have proposed that the C-C bond cleavage reaction occurs through the participation of the FeIII-O-OH species that is trapped by the electrophilic property of the carbonyl compound giving a peroxide adduct that fragments to produce an acyl-carbon cleavage. Scientific developments leading up to this conclusion are considered. In the first author's views, "The study of mechanisms is not a scientific but a cultural activity. Mechanisms do not aim at an absolute truth but are intended to be a "running" commentary on the status of knowledge in a field. As the structural knowledge in a field advances Mechanisms evolve to take note of the new findings. Just as a constructive "running" commentary provides the stimulus for higher standards of performance, so Mechanisms call for better and firmer structural information from their practitioners".
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In the citing paper
“It catalyzes the rate-limiting final step in estrogen (E) production, the hydroxylation of androstenedione to estrone and of T to E 2 (Fig. 1).”
From A new era in ovulation induction (2006) · cites this paper as [16]
In the citing paper
“Letrozole blocks the conversion of androgens to estrogen (31).”
From Effects of letrozole on superovulation with gonadotropins in women undergoing intrauterine insemination (2003) · cites this paper as [31]
In the citing paper
“Aromatase is a cytochrome P-450 enzyme complex that catalyzes the rate-limiting step in the production of estrogens (E), that is, the conversion of the androgens, androstenedione and testosterone, to estrone (E 1 ) and E 2 (9).”
From Aromatase inhibition improves ovarian response to follicle-stimulating hormone in poor responders (2002) · cites this paper as [9]
Citations
Cites
Cytochrome P-450: Structure, Mechanism, and Biochemistry
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Mechanistic studies on C-19 demethylation in oestrogen biosynthesis
Akhtar, M., Calder, M. R., Corina, D. L., & Wright, J. N. (1982) · Biochemical Journal · doi:10.1042/bj2010569 · Cited by 292
Purification and characterization of human placental aromatase cytochrome P-450.
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THE CONVERSION OF PROGESTERONE TO ANDROGENS BY TESTES
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Research works printed but not linked: 1
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Sono, M., Roach, M. P., Coulter, E. D., & Dawson, J. H. (1996) · Chemical Reviews · doi:10.1021/cr9500500 · Cited by 2,445
Structure and chemistry of cytochrome p450
Denisov, I. G., Makris, T. M., Sligar, S. G., & Schlichting, I. (2005) · Chemical Reviews · doi:10.1021/cr0307143 · Cited by 2,106
Aromatase Cytochrome P450, The Enzyme Responsible for Estrogen Biosynthesis*
SIMPSON, E. R., Mahendroo, M., Means, G., Kilgore, M. W., Hinshelwood, M. M., Graham-Lorence, S. E., Amarneh, B., Ito, Y., Fisher, C. R., Michael, M. D., et al. (1994) · Endocrine Reviews · doi:10.1210/edrv-15-3-342 · Cited by 1,542
Structural basis for androgen specificity and oestrogen synthesis in human aromatase
Ghosh, D., Griswold, J., Erman, M., & Pangborn, W. (2009) · Nature · doi:10.1038/nature07614 · Cited by 618
Aromatase inhibition improves ovarian response to follicle-stimulating hormone in poor responders
Mitwally, M. F. M., & Casper, R. F. (2002) · Fertility and Sterility · doi:10.1016/s0015-0282(01)03280-0 · Cited by 407
Metadata
- Authors
- Akhtar, M., Njar, V. C. O., & Neville Wright, J.
- Affiliations
- University of Southampton (GB)
- Corresponding author
- Akhtar, Muhammad
- Venue
- The Journal of Steroid Biochemistry and Molecular Biology
- Publisher
- Elsevier BV
- Published
- 1993-03
- Volume
- 44
- Issue
- 4-6
- Pages
- 375-387
- ISSN
- 0960-0760 (ISSN-L)
- OpenAlex
- W2015325021
- Cited by
- 193
- References
- 50
- Citations by year
- 2024: 2 · 2023: 3 · 2022: 6 · 2021: 3 · 2020: 6 · 2019: 3 · 2018: 3 · 2017: 31 · 2016: 4 · 2015: 29 · 2014: 4 · 2013: 2 · 2012: 3
- FWCI
- 5.29
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Steroid Biochemistry and Molecular Biology (publishedVersion)
- PubMed (publishedVersion)
- Zurich Open Repository and Archive (University of Zurich) (submittedVersion)
- Funders
- Wellcome Trust
- Topics
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Physical Organic Chemistry and Reaction Kinetics
- Keywords
- aromatase, cytochrome P450, C–C bond cleavage, reaction mechanism, hydroxyl radicals, heterolysis, steroid hydroxylation, alcohol oxidation
- MeSH terms
- Animals, Aromatase, Cytochrome P-450 Enzyme System, Female, Humans, Hydroxylation, Male, Models, Theoretical, Oxidation-Reduction, Substrate Specificity, Molecular Structure
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