- 関
- acylate
WordNet
- the process of introducing an acyl group into a compound
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/11/21 14:57:34」(JST)
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In chemistry, acylation (rarely, but more formally: alkanoylation) is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent.
Because they form a strong electrophile when treated with some metal catalysts, acyl halides are commonly used as acylating agents. For example, Friedel-Crafts acylation uses acetyl chloride (ethanoyl chloride), CH3COCl, as the agent and aluminum chloride (AlCl3) as a catalyst to add an ethanoyl (acetyl) group to benzene:
The mechanism of this reaction is electrophilic aromatic substitution.
Acyl halides and anhydrides of carboxylic acids are also commonly used acylating agents to acylate amines to form amides or acylate alcohols to form esters. The amines and alcohols are nucleophiles; the mechanism is a nucleophilic acyl substitution. Succinic acid is also commonly used in a specific type of acylation called succination. Oversuccination occurs when more than one succinate adds to a single compound.
Acylation can be used to prevent rearrangement reactions that would normally occur in alkylation. To do this an acylation reaction is performed, then the carbonyl is removed by clemmensen reduction or a similar process. [1]
Acylation in biology
Protein acylation is the post-translational modification of proteins via the attachment of functional groups through acyl linkages. One prominent type is fatty acylation, the addition of fatty acids to particular amino acids (e.g. myristoylation or palmitoylation).[2] Protein acylation has been observed as a mechanism of biological signaling.[3]
See also
References
- ^ Vollhardt, Peter; Schore, Neil (2014). Organic Chemistry: Structure and Function. (7th ed.). New York, NY: W.H. Freeman and Company. pp. 714–715. ISBN 978-1-4641-2027-5.
- ^ Resh, M. D. (1999). "Fatty acylation of proteins: New insights into membrane targeting of myristoylated and palmitoylated proteins". Biochimica et Biophysica Acta. 1451 (1): 1–16. doi:10.1016/S0167-4889(99)00075-0. PMID 10446384.
- ^ Towler, D A; Gordon, J I; Adams, S P; Glaser, L (1988). "The Biology and Enzymology of Eukaryotic Protein Acylation". Annual Review of Biochemistry. 57 (1): 69–97. doi:10.1146/annurev.bi.57.070188.000441.
UpToDate Contents
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English Journal
- Cyanamide-mediated Inhibition of N-acetyltransferase 1.
- Dierolf D, Scheitza S, Bonifas J, Blömeke B.SourceDepartment of Environmental Toxicology, University of Trier, Universitätsring 15, 54296 Trier, Germany.
- Toxicology.Toxicology.2012 Dec 8;302(1):1-10. doi: 10.1016/j.tox.2012.06.019. Epub 2012 Jul 24.
- Cyanamide has been used for decades for medical intentions in the treatment of alcoholism and for agricultural purposes as a plant growth regulator and bud-breaking agent. Its therapeutic effect is mediated by reversible inhibition of aldehyde dehydrogenase and it was reported to be metabolized in v
- PMID 22835378
- Modulating rheological and degradation properties of temperature-responsive gelling systems composed of blends of PCLA-PEG-PCLA triblock copolymers and their fully hexanoyl-capped derivatives.
- Petit A, Müller B, Bruin P, Meyboom R, Piest M, Kroon-Batenburg LM, de Leede LG, Hennink WE, Vermonden T.SourceInGell Labs BV, Groningen, The Netherlands; Department of Pharmaceutics, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Utrecht, The Netherlands.
- Acta biomaterialia.Acta Biomater.2012 Dec;8(12):4260-7. doi: 10.1016/j.actbio.2012.07.044. Epub 2012 Aug 6.
- In this study, the ability to modulate rheological and degradation properties of temperature-responsive gelling systems composed of aqueous blends of poly(ε-caprolactone-co-lactide)-b-poly(ethylene glycol)-b-poly(ε-caprolactone-co-lactide) (PCLA-PEG-PCLA) triblock copolymers (i.e. uncapped) and th
- PMID 22877819
Japanese Journal
- マイクロフロー光反応·イミドイル化反応·アシル化反応を駆使する効率的な有機合成
- 布施 新一郎,高橋 孝志
- 有機合成化学協会誌 73(5), 442-451, 2015
- … We have also developed efficient micro-flow photo-reaction, imidoylation, and acylation by taking the advantages of micro-flow technology. … Herein, we wish to report our synthesis of bioactive vitamin D3, its analogues and α-aryl carbonyl compounds based on the micro-flow photo-reaction as well as the synthesis of diimine ligands for olefin polymerization catalysts and peptides based on the micro-flow imidoylation and acylation. …
- NAID 130005077684
- ショッテンバウマン反応による水溶性天然高分子変換法の開発
- 松井 栄樹,吉田 竜二,内田 敦之
- 高分子論文集 72(2), 71-75, 2015
- 本研究では水溶性セルロースを誘導体化する方法として,塩基性水溶液中で反応を行うショッテンバウマン反応を選択し,水を用いた反応と後処理による環境負荷の少ない変換法の開発を目指した.まず,水溶性セルロースとしてヒドロキシエチルセルロースを選択し,飽和Na2CO3水溶液中での塩化ベンゾイルとの反応について検討を行った.目的のベンゾイル化生成物の形成についてATR-IR,13C NMRの測定により確認,同 …
- NAID 130004793193
- Facile synthesis of acyl chitosan isothiocyanates and their application to porphyrin-appended chitosan derivative.
- Shibano Masaya,Nishida Shouko,Saito Yasuko,Kamitakahara Hiroshi,Takano Toshiyuki
- Carbohydrate polymers 113, 279-285, 2014-11-26
- … The following acylation of compound 2 with hexanoyl chloride in the presence of pyridine afforded 3,6-di-O-2,3-hexanoyl chitosan isothiocyanate (4a) with a DS of the isothiocyanate groups of 0.70 in high yield, unexpectedly. …
- NAID 120005477734
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- acylation 【名】アシル化、アシレーション 分子にアシル基(RCO型の原子団、「... - アルクがお届けする進化するオンライン英和・和英辞書データベース。一般的な単語や連語から、イディオム、専門用語、スラングまで幅広く収録。
Related Pictures
★リンクテーブル★
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- acylation
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- 英
- acylation、acylate
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- deacylate
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- aminoacylate