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Chemical reaction which adds an acyl group (R–C=O) to a compound
In chemistry, acylation is a broad class of chemical reactions in which an acyl group (R−C=O) is added to a substrate. The compound providing the acyl
Acylation
S-Acylation is the process of chemically linking a molecule to another molecule via a thioester bond. Protein S-acylation is a sub-type of S-acylation where
S-Acylation
Set of reactions to attach substituents to an aromatic ring
Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution. In commercial
Friedel–Crafts_reaction
The Kostanecki acylation is a method used in organic synthesis to form chromones or coumarins by acylation of O-hydroxyaryl ketones with aliphatic acid
Kostanecki_acylation
Chemical compound
with Mander's reagent will selectively afford the C-acylation product. Thus, for enolate acylation reactions in which C- vs. O-selectivity is a concern
Methyl_cyanoformate
Protein family
resistance and lipid A acylation protein PagP is a family of several bacterial antimicrobial peptide resistance and lipid A acylation (PagP) proteins. The
Lipid_A_acylase
Reaction sequence in organic chemistry
electrophiles. Acyl halides result in the formation of 1,3-diketones (Stork acylation); and benzylic, allylic/propargylic, α-carbonyl (e.g., bromoacetone),
Stork_enamine_alkylation
Protein in humans
is present in C3adesArg form. C3adesArg is more commonly named ASP or acylation-stimulating-protein due to its marked stimulating action on triacylglycerol
Acylation_stimulating_protein
Brand name for a chemical product
demonstrated catalytic properties in alkylation, isomerization, oligomerization, acylation, ketalization, esterification, hydrolysis of sugars and ethers, and oxidation
Nafion
Chemical compound
an alternative to polyphosphoric acid in chemical synthesis to promote acylation reactions. Eaton, P. E.; Carlson, G. R.; Lee, J. T. (1973). "Phosphorus
Eaton's_reagent
Organic compound (C6H5NH2); simplest aromatic amine
Aniline (From Portuguese: anil, meaning 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula C6H5NH2. Consisting
Aniline
Chemical compounds and groups containing nitrogen with a lone pair (:N)
In chemistry, amines (/əˈmiːn, ˈæmiːn/, UK also /ˈeɪmiːn/) are organic compounds that contain carbon–nitrogen bonds. Amines are formed when one or more
Amine
Class of chemical compounds formally derived from the acylation of urea
ureides) are a class of chemical compounds formally derived from the acylation of urea. A subclass of acylureas known as benzoylureas are insecticides
Acylurea
Chemical compound
Meldrum's acid at this position, through reactions such as alkylation and acylation. For example, deprotonation and reaction with a simple alkyl halide (R−Cl)
Meldrum's_acid
Chemical compound
quickly to prevent isomerisation. HATU is commonly encountered in amine acylation reactions (i.e., amide formation). Such reactions are typically performed
HATU
Chemical reaction
aliphatic anhydrides are used, coumarins can also be formed. (See Kostanecki acylation.) The o-hydroxyaryl ketone first undergoes tautomerization to form the
Allan–Robinson_reaction
Chemical reaction which attaches an electrophile to an aromatic ring
halogenation, aromatic sulfonation, and Friedel-Crafts alkylation and acylation. The most widely practised example of this reaction is the ethylation
Electrophilic aromatic substitution
Electrophilic_aromatic_substitution
Category of polymers, in which the monomers are joined together by ester links
based synthesis, the preferred route to wholly aromatic polyesters. In acylation, the acid begins as an acyl chloride, and thus the polycondensation proceeds
Polyester
Species of fungus
antarcticus lipase can be used to catalyze the regioselective acylation of flavonoids or direct acylation with phenolic acids. Moesziomyces antarcticus contains
Moesziomyces_antarcticus
Type of chemical reaction
at temperatures of 60–110 °C. Direct acylations of alcohols with carboxylic acids is preferred over acylations with anhydrides (poor atom economy of
Fischer–Speier_esterification
Reaction in organic chemistry
the radical source used, one side-reaction is acylation, with the ratio between alkylation and acylation depending on the substrate and the reaction conditions
Minisci_reaction
Organic chemical reaction
ketones, such as those formed in a Friedel-Crafts acylation. The two-step sequence of Friedel-Crafts acylation followed by Clemmensen reduction constitutes
Clemmensen_reduction
Medication for pain and fever
alternative industrial synthesis developed at Celanese involves firstly direct acylation of phenol with acetic anhydride in the presence of hydrogen fluoride to
Paracetamol
Chemical compound
reactions typical of other simple alkyl amines, i.e. protonation, alkylation, acylation, condensation with carbonyls. Like other simple aliphatic amines, pentylamine
Pentylamine
Chemical compound
propargyl halides. The behavior of propargyl amine is illustrated by its acylation benzoyl chloride to the amide. A Sonogashira coupling of the terminal
Propargylamine
Start of a polypeptide
The N-terminus (also known as the amino-terminus, NH2-terminus, N-terminal end or amine-terminus) is the start of a protein or polypeptide, referring to
N-terminus
Organic compound of the form >C=C=O
Nahmany, Moshe; Melman, Artem (November 19, 2002) [September 1, 2002]. "Acylation through ketene intermediates". Journal of Organic Chemistry. 67 (25).
Ketene
Chemical compound
AlCl3 is a common Lewis-acid catalyst for Friedel-Crafts reactions, both acylations and alkylations. These types of reactions are the major use for aluminium
Aluminium_chloride
Principle in chemical kinetics
Curtin–Hammett principle has been invoked to explain regioselectivity in the acylation of 1,2-diols. Ordinarily, the less-hindered site of an asymmetric 1,2-diol
Curtin–Hammett_principle
Chemical compound
palmitate is also marketed as "vitamin C ester". It is synthesized by acylation of vitamin C using different acyl donors. Ascorbyl stearate Vitamin C
Ascorbyl_palmitate
Chemical compound
chloride. This synthesis can be seen as a special case of the Friedel-Crafts acylation. The reduction product is thioxanthene. Thioxanthone dissolves in concentrated
Thioxanthone
Chemical compound
liquid that is soluble in organic solvents. It is usually prepared by the acylation of benzene using valeryl chloride. Being prochiral, valerophenone undergoes
Valerophenone
Chemical compound
formed by the condensation of 1-indanone resulting from intramolecular acylation of 3-phenylpropanoic acid. Frederic Stanley Kipping was able to confirm
Truxene
Organic ring compound (C4H4NH)
3-position.[citation needed] Acylation generally occurs at the 2-position, through the use of various methods. Acylation with acid anhydrides and acid
Pyrrole
Family of various acyltransferase enzymes
involved in neutral lipid biosynthesis; enzymes involved in protein/peptide acylation; enzymes involved in phospholipid re-modelling. The structure for one
MBOAT
Class of chemical compounds
alkylation. Analogously, this reaction can be used as an effective means of acylation. A variety of alkylating and acylating agents including benzylic, allylic
Enamine
Chemical compound
acetylferrocene and bromocresol]] Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac2O): Fe(C5H5)2 + Ac2O →
Acetylferrocene
Organic compounds containing amine and carboxylic groups
1139/G10-063. PMID 20962881. Magee T, Seabra MC (April 2005). "Fatty acylation and prenylation of proteins: what's hot in fat". Current Opinion in Cell
Amino_acid
Chemical reaction
aromatic sulfonation and acylation and alkylating Friedel-Crafts reactions. It further consists of alkylation and acylation. In electrophilic substitution
Electrophilic_substitution
American chemist
chemist, mostly known for developing the Friedel–Crafts alkylation and acylation reactions with Charles Friedel in 1876. A research chemist for most of
James_Crafts
Chemical compound
Chemical synthesis can be effectively carried out by conducting an N-acylation reaction on 1-aminocyclopropanol. Treatment of isocyanatocyclopropane
Coprine
Method of separating enantiomers in a racemic mixture by reaction rate
resolution acylation of amines. With 10 mol% (-)-PPY* in chloroform at –50 °C, good to very good selectivities were observed in the acylation of amines
Kinetic_resolution
Chemical compound
chloride of dichloroacetic acid. It is a colourless liquid and is used in acylation reactions. Unlike typical acid chlorides, which are often prepared from
Dichloroacetyl_chloride
Chemical compound
Isatin N-alkylation, acylation
Isatin
Chemical compound
be synthetically produced from propiophenone through a Friedel-Crafts acylation of propionic acid and benzene. The resulting propiophenone can be brominated
Cathinone
Chemical compound
prepared by one of three methods: amide bond formation, N-alkylation and C-acylation. Most commonly 2,5-diketopiperazines are generated by cyclisation of dipeptides
2,5-Diketopiperazine
Chemical compound
formation of carbon monoxide) upon heating. Yet another reaction involves the acylation of triphenylalkelynephosphoranes. (C6H5)3P=CHR + R'−CO−Im → (C6H5)3P+−CHR−COR'
Carbonyldiimidazole
Glycoprotein present in some enveloped viruses
and R domains of the HE enzyme also influence intracellular transport. Acylation of the hemagglutinin-esterase has shown to play an essential role in virus
Hemagglutinin_esterase
Post-translational modification
the cytosol of the cell. As a fatty acylation reaction, protein palmitoylation is classified as both an acylation and a lipidation post-translational
Palmitoylation
Chemical compound
derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis. On a two-dimensional
Ferrocenecarboxylic_acid
Class of enzymes
primarily known for catalyzing the acylation of monolysocardiolipin back into cardiolipin, although it does catalyze the acylation of other polyglycerophospholipids
Acyl-CoA:lysocardiolipin acyltransferase-1
Acyl-CoA:lysocardiolipin_acyltransferase-1
Nonsteroidal anti-inflammatory drug
synthesis took six steps. Firstly, isobutylbenzene undergoes Friedel-Crafts acylation with acetic anhydride, yielding p-isobutylphenyl methyl ketone. Then,
Ibuprofen
Chemical compound
undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidation
Ethylamine
Chemical compound
6-dimethoxy-1,3,5-triazine (CDMT) is a triazine derivative commonly used in acylation reactions for the synthesis of amides and esters as well as for activation
2-Chloro-4,6-dimethoxy-1,3,5-triazine
2-Chloro-4,6-dimethoxy-1,3,5-triazine
Chemical compound
be prepared from 4-hydroxybenzaldehyde, by vinylation of phenols, or acylation of polystyrene followed by oxidation at room temperature. If poly(4-methoxystyrene)
Poly(4-vinylphenol)
Chemical compound
promote reactions of carboxylic acids, including Friedel-Crafts acylation and acylation of other unsaturated compounds. Other electrophilic aromatic substitution
Trifluoroacetic_anhydride
Chemical compound
anhydride can react with aromatics such as benzene via Friedel-Crafts acylation. This always happens in such a way that the ring opening occurs at the
Itaconic_anhydride
Chemical compound
the ring. Many groups can be attached to the ring, via halogenation, acylation, sulfonation, and related processes. Phenol is so strongly activated that
Phenol
Chemical reaction named after its discoverers or developers
reaction, the Wittig reaction, the Claisen condensation, the Friedel–Crafts acylation, and the Diels–Alder reaction. Books have been published devoted exclusively
Name_reaction
Chemical drug alteration process
them into the lead structures. O-alkylation, N-alkylation, O-acylation and N-acylation reactions are used to introduce both acidic and basic groups.
Molecular_modification
Co- & Post-translational modification
cytoplasm of cells. This lipidation event is the most common type of fatty acylation and is present in many organisms, including animals, plants, fungi, protozoans
Myristoylation
Chemical compound
W.; Vorbrüggen, H. (1978). "4-Dialkylaminopyridines as Highly Active Acylation Catalysts". Angew. Chem. Int. Ed. Engl. 17 (8): 569–583. doi:10.1002/anie
4-Dimethylaminopyridine
Error correction in biochemical reactions
1976). "Direct experimental evidence for kinetic proofreading in amino acylation of tRNAIle". Proc. Natl. Acad. Sci. U.S.A. 73 (4): 1164–8. Bibcode:1976PNAS
Kinetic_proofreading
Chemical compound
Hexanoyl chloride is a six-carbon acyl chloride with a straight-chain structure that is used as a reagent in organic synthesis. Hexanoyl chloride consists
Hexanoyl_chloride
Compound derived from an acid
also react with water, anhydrous conditions are preferred. The analogous acylations of amines to give amides are less sensitive because amines are stronger
Ester
Chemical compound
Knoevenagel condensation reactions with aldehydes and ketones and also acylation reactions. The 1,3-dimethylbarbituric acid substructure motif has found
1,3-Dimethylbarbituric_acid
Chemical changes in proteins following their translation from mRNA
(eukaryotic) and aIF5A (archaeal) (see above). acylation, e.g. O-acylation (esters), N-acylation (amides), S-acylation (thioesters) acetylation, the addition
Post-translational modification
Post-translational_modification
Chemical compound
(SnCl4) allows significantly shorter reaction times than the Friedel-Crafts acylation with 4-phenylbutanoic acid. 4-Phenylbutanoic acid chlorides with electron-donating
1-Tetralone
Protein-coding gene in humans
Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine". Journal of Medicinal Chemistry. 64 (14):
GPR174
Extremely strong acid
used for alkylating benzene with ethene and propene as well as difficult acylations, e.g. of chlorobenzene. In organic chemistry, superacids are used as a
Superacid
Class of organic compounds
intermediate). Bases, such as pyridine or N,N-dimethylformamide, catalyze acylations. These reagents activate the acyl chloride via a nucleophilic catalysis
Acyl_chloride
Chemical compound
Y, Berg JA, Gygi JP, Gygi SP, Winge DR, Rutter J (August 2018). "ACP Acylation Is an Acetyl-CoA-Dependent Modification Required for Electron Transport
Acetyl-CoA
Chemical compound
add in conjugate to give the corresponding phospholene. Friedel-Crafts acylation occurs to phospholes coordinated to =Mo(CO)5, but not Vilsmeier-Haack
Phosphole
Reaction that converts amino acids into a keto-amides
confused with the Dakin reaction. The reaction mechanism involves the acylation and activation of the acid 1 to the mixed anhydride 3. The amide will
Dakin–West_reaction
Acid that is insoluble in the reaction medium
alkylamines are prepared by amination of alcohols, catalyzed by solid acids. Acylations are also catalyzed by solid acids. Solid acids can be used as electrolytes
Solid_acid
Organic compounds with a –COOH group and a C=O group
precursors to the same. Alpha-keto acids possesses extensive chemistry as acylation agents. Furthermore, alpha-keto acids such as phenylpyruvic acid are endogenous
Keto_acid
Class of organic compounds
halides. For example, chloroformylation, a specific type of Friedel-Crafts acylation which uses formaldehyde as a reagent[citation needed], or by the direct
Acyl_halide
Chemical compound
used as a tear gas. Phenacyl chloride is synthesized in a Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst: With anisole, it is used
Chloroacetyl_chloride
Group of chemical compounds
and amides (1.20–1.21 Å). They are reactive reagents for halogenation, acylation and dehydration reactions. Wikimedia Commons has media related to Carbon
Carbon_oxohalide
Chemical compound
the process is the production of 2,6-difluorobenzoyl isocyanate in an acylation reaction using 2,6-difluorobenzamide and oxalyl dichloride. The final
Novaluron
Chemical compound
acid chloride and treated with stannic chloride to effect Friedel-Crafts acylation to give enone 3. Hydride reduction, selective oxidation of the allylic
Ptaquiloside
Chemical compound
(1976). "New horizons in carbonyl chemistry: reagents for nucleophilic acylation". Tetrahedron. 32 (16): 1943–1971. doi:10.1016/0040-4020(76)80088-9. Soderquist
Methyl_vinyl_ether
Organic compounds of the form >C=O
organometallic reagents. Aryl ketones can be prepared in the Friedel–Crafts acylation, the related Houben–Hoesch reaction, and the Fries rearrangement. Ozonolysis
Ketone
Class of organic compounds used as dye
pre-existing azo compounds. Typical reactions include metal complexation and acylation. Illustrative azo dyes or their precursors Direct Brown 78 Direct Blue
Azo_dye
Dicarboxylic acid
biodegradable polymers, which are of interest in tissue engineering applications. Acylation with succinic acid is called succination. Oversuccination occurs when
Succinic_acid
Chemical reaction
Seebach Umpolung is a name reaction of organic chemistry that allows for acylation by converting aldehydes into lithiated 1,3-dithianes. The lithiated 1
Corey–Seebach_reaction
Post-translational modification
(CPS1) of the urea cycle with 31 sites. In the context of other lysine acylations, malonylation can be positioned as follows: While acetylation neutralizes
Lysine_malonylation
Chemical element with atomic number 53 (I)
December 2008. Polgár L (August 1979). "Deuterium isotope effects on papain acylation. Evidence for lack of general base catalysis and for enzyme–leaving-group
Iodine
Antihypotensive medication
enantiomers, making it a racemate; i.e., a 1:1 mixture of (R)- and (S)-forms: Acylation of 1,4-dimethoxybenzene with chloroacetyl chloride gives the chloroketone
Midodrine
Vitamin
be transformed to succinyl-CoA in the cycle. CoA is also required for acylation and acetylation, which, for example, are involved in signal transduction
Pantothenic_acid
German chemist (born 1933)
Helmut Vorbrüggen (1978). "4-Dialkylaminopyridines as Highly Active Acylation Catalysts. [New synthetic method (25)]". Angewandte Chemie International
Wolfgang_Steglich
Chemical compound
2-benziodoxol-3(1H)-one. The target compound can then be obtained by acylation with acetic anhydride and subsequent substitution reaction with
Togni_reagent_II
Trace amine
chain to the phenyl ring is possible. This can be done via Friedel-Crafts acylation with N-protected acyl chlorides when the arene is activated, or by Heck
Phenethylamine
Chemical compound
novel derivatives continue to appear. Mirfentanil was synthesized via acylation of the product of the reaction of 2-chloropyrazine and 1-(2-phenylethyl)-4-piperidinone
Mirfentanil
Chemical compound
solid triflic acid equivalent for Friedel–Crafts hydroxyalkylation and acylation". Journal of Fluorine Chemistry. 171: 102–112. Bibcode:2015JFluC.171.
Diphenylacetic_acid
Signaling molecule
series of enzymatic reactions. De novo synthesis of PI starts with an acylation process of glyceraldehyde 3-phosphate (G-3-P) by GPAT enzymes at the sn-1
Phosphatidylinositol
combines the Cannizzaro disproportionation with a directed Friedel-Crafts acylation. In Casiraghi's original 1978 formulation, Grignard reagents served as
Casiraghi_formylation
Chemical compound
One specific application of 4-chlorophenyl azide is in Friedel Crafts acylation and alkylation. The azide on 4-chlorophenyl azide acts as an electron
4-Chlorophenyl_azide
Group of chemical compounds
Niels; Diep, Thi Ai; Janfelt, Christian; Hansen, Harald Severin (2012). "N-acylation of phosphatidylethanolamine and its biological functions in mammals".
Phosphatidylethanolamine
Chemical compound
the reactive protonated nitrogen, followed by successive ring-opening acylation of the primary amine results in the formation of the polyamide. The ring-opening
Laurolactam
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