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Acetyl

Not to be confused with Acetal.
Acetyl
Skeletal formula of acetyl with all implicit hydrogens shown
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IUPAC name
Acetyl (preferred to ethanoyl)[1][2]
Systematic IUPAC name
Methyloxidocarbon(•)[3] (additive)
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Abbreviations Ac
1697938
3170-69-2 7pxN
ChEBI CHEBI:46887 7pxY
ChemSpider 121499 7pxY
786
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
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C2H3O
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
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−15 to −9 kJ mol−1
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Related compounds
Acetone

Carbon monoxide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN verify (what is10pxY/10pxN?)
Infobox references

In organic chemistry, acetyl is a functional group, the acyl with chemical formula COCH3. It is sometimes represented by the symbol Ac[4] (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. The acetyl moiety is a component of many organic compounds, including the neurotransmitter acetylcholine, acetyl-CoA, acetylcysteine, and the analgesics 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 coenzyme A (CoA). Acetyl-CoA is an intermediate both in the biological synthesis and in the breakdown of many organic molecules. Acetyl-CoA is also created during the second stage of cellular respiration, the Krebs Cycle. It is formed from pyruvic acid with the help of water and is later bonded to a pre-existing four-carbon molecule to carry out the Krebs Cycle.

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.[5] 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.

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:[6]

H2NCH2CO2H + (CH3CO)2O → CH3C(O)NHCH2CO2H + CH3CO2H

Pharmacology

Acetylated organic molecules exhibit increased ability to cross the selectively permeable blood–brain barrier. 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. 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.[7] Acetylation of resveratrol holds promise as one of the first anti-radiation medicines for human populations.[8]

See also

References

  1. ^ "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. 
  2. ^ "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. 
  3. ^ "Acetyl". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 
  4. ^ Hanson, James A. (2001). Functional group chemistry. Cambridge, Eng: Royal Society of Chemistry. p. 11. ISBN 0-85404-627-5. 
  5. ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  6. ^ R. M. Herbst and D. Shemin (1943). "Acetylglycine". Org. Synth. ; Coll. Vol. 2, p. 11 
  7. ^ 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: 117–31. PMID 15591009. doi:10.1196/annals.1320.011.  edit
  8. ^ Koide, Kazunori, et al. "The Use of 3, 5, 4′-Tri-O-acetylresveratrol as a Potential Prodrug for Resveratrol Protects Mice from γ-Irradiation-Induced Death." ACS medicinal chemistry letters 2.4 (2011): 270-274. http://pubs.acs.org/doi/abs/10.1021/ml100159p