Acetyl group
 | This article needs additional citations for verification. (January 2016) |
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| Names | |
|---|---|
| IUPAC name | |
| Systematic IUPAC name
Methyloxidocarbon(•)[4] (additive) | |
| Identifiers | |
3D model (JSmol)
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| Abbreviations | Ac |
| 1697938 | |
| ChEBI | |
| ChemSpider | |
| 786 | |
PubChem CID
|
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| Properties | |
| C2H3O | |
| Molar mass | 43.045 g·mol−1 |
| Thermochemistry | |
Std enthalpy of
formation (ΔfH⦵298) |
−15 to −9 kJ mol−1 |
| Related compounds | |
Related compounds
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Acetone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In organic chemistry, acetyl is a moiety, the acyl with chemical formula CH3CO. It is sometimes represented by the symbol Ac[5] (not to be confused with the element actinium).
The acetyl group contains a methyl group single-bonded to a carbonyl. The carbonyl center of an acyl radical has one nonbonded electron with which it forms a chemical bond to the remainder R of the molecule. In IUPAC nomenclature, acetyl is called ethanoyl, although this term is rarely heard.[citation needed]
The acetyl moiety is a component of many organic compounds, including acetic acid, the neurotransmitter acetylcholine, acetyl-CoA, acetylcysteine, acetaminophen (also known as paracetamol), and acetylsalicylic acid (better known as aspirin).
Acetylation
In nature
The introduction of an acetyl group into a molecule is called acetylation. In biological organisms, acetyl groups are commonly transferred from acetyl-CoA to other organic molecules. Acetyl-CoA is an intermediate both in the biological synthetase and in the breakdown of many organic molecules. Acetyl-CoA is also created during the second stage of cellular respiration, the Krebs Cycle, by the action of pyruvate dehydrogenase on pyruvic acid.
Histones and other proteins are often modified by acetylation. For example, on the DNA level, histone acetylation by acetyltransferases (HATs) causes an expansion of chromatin architecture, allowing for genetic transcription to occur. However, removal of the acetyl group by histone deacetylases (HDACs) condenses DNA structure, thereby preventing transcription.[6] In addition to HDACs, Methyl group additions are able to bind DNA resulting in DNA methylation, and this is another common way to block DNA acetylation and inhibit gene transcription.[7]
Synthetic organic and pharmaceutical chemistry
Acetylation can be achieved using a variety of methods, the most common one being via the use of acetic anhydride or acetyl chloride, often in the presence of a tertiary or aromatic amine base. A typical acetylation is the conversion of glycine to N-acetylglycine:[8]
- H2NCH2CO2H + (CH3CO)2O → CH3C(O)NHCH2CO2H + CH3CO2H
Pharmacology
Acetylated organic molecules exhibit increased ability to cross the selectively permeable blood–brain barrier.[citation needed] Acetylation helps a given drug reach the brain more quickly, making the drug's effects more intense and increasing the effectiveness of a given dose.[citation needed] The acetyl group in acetylsalicylic acid (aspirin) enhances its effectiveness relative to the natural anti-inflammatant salicylic acid. In similar manner, acetylation converts the natural painkiller morphine into the far more potent heroin (diacetylmorphine).
There is some evidence that acetyl-L-carnitine may be more effective for some applications than L-carnitine.[9] Acetylation of resveratrol holds promise as one of the first anti-radiation medicines for human populations.[10]
See also
- Acetaldehyde
- Acetoxy group
- Histone acetylation and deacetylation
- Polyoxymethylene plastic, a.k.a. acetal resin, a thermoplastic
References
- ^ "List of Radical Names Beginning from "A"". Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. Copyright 1979 IUPAC.
- ^ "R-5.7.1 Carboxylic acids, where acetyl appears as an example". IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), 1993, Blackwell Scientific publications, Copyright 1993 IUPAC.
- ^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-65.1.7.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
- ^ "Acetyl". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute.
- ^ Hanson, James A. (2001). Functional group chemistry. Cambridge, Eng: Royal Society of Chemistry. p. 11. ISBN 0-85404-627-5.
- ^ Cox, David L. Nelson, Michael M. (2000). Lehninger principles of biochemistry (3rd ed.). New York: Worth Publishers. ISBN 1-57259-153-6.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ Moore, Lisa D.; Le, Thuc; Fan, Guoping (2013). "DNA Methylation & Its Basic Function". Crosstalk of DNA Methylation & Other Epigenetic Mechanisms. Neuropsychopharmacology. 38 (1): 23–38. doi:10.1038/npp.2012.112. PMC 3521964. PMID 22781841.
Dnmt1 and Dnmt3b can both bind to histone deacetylases that remove acetylation from histones to make DNA pack more tightly and restrict access for transcription.
- ^ R. M. Herbst and D. Shemin (1943). "Acetylglycine". Organic Syntheses; Collected Volumes, vol. 2, p. 11.
- ^ Liu, J; Head, E; Kuratsune, H; Cotman, C. W.; Ames, B. N. (2004). "Comparison of the effects of L-carnitine and acetyl-L-carnitine on carnitine levels, ambulatory activity, and oxidative stress biomarkers in the brain of old rats". Annals of the New York Academy of Sciences. 1033 (1): 117–31. Bibcode:2004NYASA1033..117L. doi:10.1196/annals.1320.011. PMID 15591009. S2CID 24221474.
- ^ Koide, Kazunori; Osman, Sami; Garner, Amanda L.; Song, Fengling; Dixon, Tracy; Greenberger, Joel S.; Epperly, Michael W. (14 April 2011). "The Use of 3,5,4′-Tri-acetylresveratrol as a Potential Prodrug for Resveratrol Protects Mice from γ-Irradiation-Induced Death". ACS Medicinal Chemistry Letters. 2 (4): 270–274. doi:10.1021/ml100159p. PMC 3151144. PMID 21826253.