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アセチル化する

関: acetylation

WordNet

receive substitution of an acetyl group; "the compounds acetylated" (同)acetylize, acetylise
introduce an acetyl group into (a chemical compound) (同)acetylize, acetylise
the process of introducing an acetyl group into a compound; "the acetylation of cyclooxygenase-2 by aspirin"

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/18 13:14:31」(JST)

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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]

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.
^ "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.
^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
^ R. M. Herbst and D. Shemin (1943), "Acetylglycine", Org. Synth. ; Coll. Vol. 2: 11
^ http://www.ncbi.nlm.nih.gov/pubmed/15591009
^ 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

UpToDate Contents

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1. アスピリン：リウマチ性疾患における作用機序、主な毒性、および使用 aspirin mechanism of action major toxicities and use in rheumatic diseases
2. 非選択性非ステロイド性抗炎症剤（NSAIDs）：心血管系への有害作用 nonselective nsaids adverse cardiovascular effects
3. 発作性夜間血色素尿症の病因：GPIアンカーの欠如 pathogenesis of paroxysmal nocturnal hemoglobinuria absence of the gpi anchor

English Journal

The N-terminal Acetyltransferase Naa10/ARD1 Does Not Acetylate Lysine Residues.

Magin RS1, March ZM2, Marmorstein R3.
The Journal of biological chemistry.J Biol Chem.2016 Mar 4;291(10):5270-7. doi: 10.1074/jbc.M115.709428. Epub 2016 Jan 11.
The N-terminal acetyltransferase NatA is a heterodimeric complex consisting of a catalytic subunit (Naa10/ARD1) and an auxiliary subunit (Naa15). NatA co-translationally acetylates the N termini of a wide variety of nascent polypeptides. In addition, Naa10 can act independently to posttranslationall
PMID 26755727

Improved proteostasis in the secretory pathway rescues Alzheimer's disease in the mouse.

Peng Y1, Kim MJ2, Hullinger R3, O'Riordan KJ4, Burger C5, Pehar M6, Puglielli L7.
Brain : a journal of neurology.Brain.2016 Mar;139(Pt 3):937-52. doi: 10.1093/brain/awv385. Epub 2016 Jan 19.
See Duran-Aniotz et al. (doi:10.1093/brain/awv401) for a scientific commentary on this article.The aberrant accumulation of toxic protein aggregates is a key feature of many neurodegenerative diseases, including Huntington's disease, amyotrophic lateral sclerosis and Alzheimer's disease. As such, im
PMID 26787453

A peptide tetramer Tk-tPN induces tolerance of cardiac allografting by conversion of type 1 to type 2 immune responses via the Toll-like receptor 2 signal-promoted activation of the MCP1 gene.

Li Z1, Yang N2, Zhou L1, Gu P2, Wang H3, Zhou Y1, Zhou P3, Lu L1, Chou KY2.
Immunology.Immunology.2016 Mar;147(3):355-66. doi: 10.1111/imm.12569.
The plant protein trichosanthin (Tk) and its derived peptide tetramer Tk-tPN have been shown to stimulate the type 2 immune responses for treating autoimmune disease. This work explores the possibility of using Tk-tPN as a non-toxic immunosuppressant to induce transplantation tolerance using the mec
PMID 26694804

Sororin actively maintains sister chromatid cohesion.

Ladurner R1, Kreidl E1, Ivanov MP1, Ekker H2, Idarraga-Amado MH1, Busslinger GA1, Wutz G1, Cisneros DA1, Peters JM3.
The EMBO journal.EMBO J.2016 Feb 22. pii: e201592532. [Epub ahead of print]
Cohesion between sister chromatids is established during DNA replication but needs to be maintained to enable proper chromosome-spindle attachments in mitosis or meiosis. Cohesion is mediated by cohesin, but also depends on cohesin acetylation and sororin. Sororin contributes to cohesion by stabiliz
PMID 26903600

Japanese Journal

Histone Modifications Induced by Chemicals and Photogenotoxicity

Genes and Environment 36(3), 111-117, 2014
NAID 130004481213

N^a Selective Acetylation of Peptides

Mass spectrometry 1, A0010, 2012-12-01
NAID 10031126347

Bisbenzamidine derivative, pentamidine represses DNA damage response through inhibition of histone H2A acetylation.

Molecular cancer 9, 2010-02-09
NAID 120002515185

εOverexpression and Characterization of an Aminoglycoside 6'-N-Acetyltransferase with Broad Specificity from an ε-Poly-L-lysine Producer, Streptomyces albulus IFO 14147

The Journal of Biochemistry 136(4), 517-524, 2004
NAID 130003534751

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★リンクテーブル★

リンク元	「acetylation」
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「acetylation」

Acetyl
	IUPAC name Acetyl (preferred to ethanoyl)
	Systematic name Methyloxidocarbon(•) (additive)
Identifiers
Abbreviations	Ac
CAS number	3170-69-2
PubChem	137849
ChemSpider	121499
ChEBI	CHEBI:46887
Beilstein Reference	1697938
Gmelin Reference	786
Jmol-3D images	Image 1
	SMILES C[C]=O ;
	InChI InChI=1S/C2H3O/c1-2-3/h1H3 ; Key: TUCNEACPLKLKNU-UHFFFAOYSA-N ;
Properties
Molecular formula	C2H3O
Molar mass	43.04 g mol−1
Thermochemistry
Std enthalpy of; formation ΔfHo298	−15 to −9 kJ mol−1
Related compounds
Related compounds	Acetone; Carbon monoxide
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

　　[★]

n.

アセチル化

関: acetylate

「hyperacetylated」

　　[★]

高アセチル化の、過剰アセチル化した

関: hyperacetylation

「deacetylate」

　　[★]

脱アセチルする、脱アセチル化する

関: deacetylation

[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.

[isbn0-85404-627-5-4] 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: 11

[7] ttp://www.ncbi.nlm.nih.gov/pubmed/15591009

[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

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acetylate