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Topic: Amide hydrolysis


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In the News (Sun 23 Nov 14)

  
 [No title]
Amides are commonly formed from the reaction of a carboxylic acids with an amine.This is the reaction that forms peptide bonds between amino acids.
Cyclic amides are synthesized in the Beckmann rearrangement from oximes.
Amide linkages constitute a defining molecular feature of proteins, the secondary structure of which is due in part to the hydrogen bonding abilities of amides.
www.algebra.com /~pavlovd/wiki/Amide   (365 words)

  
 Amide
Amides are the members of a group of chemical compounds containing nitrogen.
Specifically, an amide is a derivative of a carboxylic acid in which the hydroxyl group has been replaced by an amine or ammonia.
Amides are commonly formed from the reaction of a carboxylic acids with an amine:
www.amide.net   (259 words)

  
  Stability Of Drugs:Mechanisms Of Degradation Hydrolysis,Oxidation, Photolysis - Pharmpedia
The hydrolysis of an ester into a mixture of an acid and alcohol involves the rupture of a covalent bond between a carbon atom and oxygen atom.
The alkaline hydrolysis of an ester is irreversible and an acid hydrolysis is reversible.
The rate of degradation of the amide group by hydrolysis is dependent on the characteristics of the substituents R1, R2 and R3.
www.pharmpedia.com /Stability_Of_Drugs:Mechanisms_Of_Degradation_Hydrolysis,Oxidation,_Photolysis   (1996 words)

  
  Amide - Wikipedia, the free encyclopedia
The amide anion is the conjugate base of ammonia, NH It is an extremely strong base, due to the extreme weakness of ammonia as a Brønsted acid.
An amide linkage is kinetically stable to hydrolysis.
Amide linkages constitute a defining molecular feature of proteins, the secondary structure of which is due in part to the hydrogen bonding abilities of amides.
en.wikipedia.org /wiki/Amide   (327 words)

  
 amide   (Site not responding. Last check: 2007-10-14)
Amide is either a functional group in organic chemistry, or an anion.
Thus, the amide anion is NH It is an extremely strong base, due to the extreme weakness of ammonia as a Bronsted acid.
Specifically, an amide results from an acid, in which a carbon atom is double bonded to oxygen and also to an hydroxyl group, when the hydroxyl group is replaced by an amine.
www.yourencyclopedia.net /Amide.html   (323 words)

  
 Encyclopedia: Amide
Amides are commonly formed from the reaction of a carboxylic acids with an amine: Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH.
Unlike the hydrolysis of esters, the kinetics of amide hydrolysis is third order- first order with respect to the amide and second order with respect to hydroxide.
Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water.
www.nationmaster.com /encyclopedia/Amide   (993 words)

  
 AMIDE FACTS AND INFORMATION   (Site not responding. Last check: 2007-10-14)
The amide anion is the conjugate_base of ammonia, NH It is an extremely strong base, due to the extreme weakness of ammonia as a Brønsted_acid.
Specifically, an amide is a derivative of a carboxylic_acid in which the hydroxyl group has been replaced by an amine or ammonia.
Amides are commonly formed from the reaction of a carboxylic_acids with an amine:
www.witwib.com /index.php?s=amide   (302 words)

  
 Amide hydrolysis
Hydrolysis of the amide bond is a major target of research in catalytic antibodies.
In amide hydrolysis breakdown of the tetrahedral intermediate is usually the rate determining step and protonation of the leaving amine is required.
We have found that the hydrolysis of heterocyclic amides of indole is accelerated by monoclonal antibodies raised against sulphonamide haptens.
www.dsch.univ.trieste.it /~benedetti/amide.htm   (340 words)

  
 Enzymes in Organic Chemistry:S.M.Roberts
Subsequent two-step hydrolysis of (14) leads to L-(S)-tert-leucine (15), an important amino acid that is used in therapeutic peptides and as a chiral auxilliary (Scheme 2) (Turner, 1995).
This type of hydrolysis is commercially important in the preparation of 6-amino-penicillanic acid and in the synthesis of some optically pure amino-acids.
The hydrolysis of nitrile groups using hydratase enzymes is of great interest to many synthetic organic chemists, principally because the hydrolysis takes place under very mild conditions (for a recent review see Crosby et al.
www.ch.ic.ac.uk /ectoc/papers/04/3-Hydrolases.html   (1224 words)

  
 Amide Summary
Amides are hydrolysed to ammonium salts with catalysis by acids or alkalis.
This lack of basicity is explained by the electron-withdrawing nature of the carbonyl group, where the lone pair on the nitrogen is delocalized by resonance, forming a partial double bond with the carbonyl carbon and putting a negative charge on the oxygen, and discussed in the peptide bond article.
Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Ester • Ether • Haloalkane • Imine • Isocyanide • Isocyanate • Ketone • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioether • Thiol • Toluene derivative
www.bookrags.com /Amide   (1091 words)

  
 A Novel Amidase (Half-Amidase) for Half-Amide Hydrolysis Involved in the Bacterial Metabolism of Cyclic Imides -- Soong ...
A Novel Amidase (Half-Amidase) for Half-Amide Hydrolysis Involved in the Bacterial Metabolism of Cyclic Imides -- Soong et al.
A Novel Amidase (Half-Amidase) for Half-Amide Hydrolysis Involved in the Bacterial Metabolism of Cyclic Imides
amide compounds which are conventional substrates and inducers
aem.asm.org /cgi/content/abstract/66/5/1947   (229 words)

  
 Strong Base - Strong Savings
However, it is also possible to suppress hydrolysis of water-sensitive compounds under PTC conditions, primarily in systems in which hydroxide (or other base) has a choice between acting as a base or as a nucleophile.
The fundamental concept is to use the phase boundary to "protect" the ester (or much more water-sensitive compounds, such as phosgene) from the base and water, to minimize non-catalyzed interfacial hydrolysis and regulate the desired reaction using the phase transfer catalyst.
Often, the design of such systems is not easy and usually requires significant expertise (extensive trial-and-error experimentation may not be effective) to carefully choose the right combination of solvent, ionic strength, catalyst, agitation, physical form of the base and other process parameters.
www.ptcorganics.com /StrongBase.htm   (1554 words)

  
 Definition of Amide hydrolysis
Amide hydrolysis involves the C-N bond being broken in reaction with water (hydrolysis).
The amide is heated under reflux with moderately concentrated acqueous acid or alkali.
The list of authors can be found here.
www.wordiq.com /definition/Amide_hydrolysis   (128 words)

  
 Ch20 : Amide hydrolysis
Amides hydrolyse to the parent carboxylic acid and the appropriate amine.
Note that the acid catalysed mechanism is analogous to the acid catalysed hydrolysis of esters.
The mechanism is an example of the less reactive system type.
www.chem.ucalgary.ca /courses/351/Carey5th/Ch20/ch20-3-4-1.html   (192 words)

  
 A Novel Amidase (Half-Amidase) for Half-Amide Hydrolysis Involved in the Bacterial Metabolism of Cyclic Imides -- Soong ...
Cyclic imide is a kind of cyclic amide, and the metabolism of cyclic imides has been studied in relation to the detoxification
Amide compounds which act as substrates and inducers of known amidase (acetamide and lactamide for the amidase of Pseudomonas
The amide compounds judged to be inactive as substrates are some short- and long-chain amides, aromatic amides, amino acid
aem.asm.org /cgi/content/full/66/5/1947   (2539 words)

  
 Molecular characterization of human and mouse fatty acid amide hydrolases -- Giang and Cravatt 94 (6): 2238 -- ...
Fatty acid amides represent a growing family of bioactive lipids with diverse cellular and physiological effects (1-5).
substrates, and palmitic and stearic amide being hydrolyzed at
Expression and regulation of the fatty acid amide hydrolase gene in the rat uterus during the estrous cycle and peri-implantation period
www.pnas.org /cgi/content/full/94/6/2238   (4545 words)

  
 Amides Menu
An introduction to amides including their physical properties.
The hydrolysis of amides using acids or alkalis (including the test for an amide).
The lack of base character in amides, the dehydration of amides to make nitriles, and the Hofmann degradation of amides to make primary amines with one less carbon atom.
www.chemguide.co.uk /organicprops/amidemenu.html   (80 words)

  
 Wiley-VCH - Greenberg, Arthur / Breneman, Curt M. / Liebman, Joel F. (eds.) - The Amide Linkage
One of the most fundamental and widespread chemical bonds in nature, the amide linkage underlies the properties of a vast array of organic molecules, polymers, and materials, including peptides and proteins.
The Amide Linkage as a Ligand-Its Properties and the Role of Distortion (A. Greenberg).
The Role of Amides in the Noncovalent Synthesis of Supramolecular Structures in Solution, at Interfaces, and in Solids (G. Palmore & J. MacDonald).
www.wiley-vch.de /publish/en/books/bySubjectCH00/bySubSubjectCH15/0-471-35893-2/?sID=25f1c856893d417cbe880637be076dba   (317 words)

  
 Conformational Effects in Enzyme Catalysis: Reaction via a High Energy Conformation in Fatty Acid Amide Hydrolase -- ...
Conformational Effects in Enzyme Catalysis: Reaction via a High Energy Conformation in Fatty Acid Amide Hydrolase -- Lodola et al.
(amide hydrolysis) occurs via a distinct, high energy conformation.
amide hydrolase, a key enzyme in the endocannabinoid system.
www.biophysj.org /cgi/content/abstract/92/2/L20   (200 words)

  
 Acetaminophen amide hydrolysis
Hey I looked around through some papers to see what sort of conditions the amide group would hydrolyze at and I found this paper " Studies of the Thermal Degradation of Acetaminophen Using a Conventional HPLC Approach and Electrospray Ionization-Mass Spectrometry"..
It would have been really helpful except its not available online and I dont have access to the resources for the hardcopy at the moment.
I figure its fairly stable compared to most amides due to the electron donating effect of the hydroxy group but I would like some specific pHs and temperatures if its possible..
www.chemicalforums.com /index.php?topic=17551.0   (280 words)

  
 Amide   (Site not responding. Last check: 2007-10-14)
Amides are the members of a group of chemicalcompounds containing nitrogen.
Specifically, an amide results from an acid, inwhich a carbon atom is double bonded to oxygen and also to an hydroxyl group, when the hydroxyl group is replaced by an amine.
Amide linkages constitute a defining molecular feature of proteins, the secondary structure of which isdue in part to the hydrogen bonding abilities of amides.
www.therfcc.org /amide-22100.html   (271 words)

  
 Amide   (Site not responding. Last check: 2007-10-14)
It may refer to a certain inorganic anion.
The amide anion is the conjugate base of ammonia, NH It is an extremely strong base, due to the extreme weakness of ammonia as a Bronsted acid.
Amides can be broken down in amide hydrolysis.
www.yotor.com /wiki/en/am/Amide.htm   (286 words)

  
 Rhodes University
The compounds used as substrates in the investigation are all essentially amides.
Thus, the ability of the strains to hydrolyze imides, hydantoins, and amides, was investigated.
Nitrile hydrolysis was demonstrated to be inducible in all three strains, and the enzyme system responsible for nitrile hydrolysis was proposed to be a nitrile hydratase-amidase system.
www.ru.ac.za /library/theses/2000/skepu   (863 words)

  
 X-ray snapshots of serine protease catalysis reveal a tetrahedral intermediate - Nature Structural & Molecular ...
An oxyanion hole, consisting of the peptide amide of the active site serine and a neighbouring glycine, was identified, and hydrogen bonding in the oxyanion hole was suggested to stabilize the two proposed tetrahedral intermediates on the catalytic pathway.
Similarly, the distances from the amide nitrogens of Gly 193 and Ser 195 to the hydroxyl oxygen of the tetrahedral intermediate were 3.1 Å and 3.9 Å, respectively.
During deacylation the distance from the amide nitrogen of Ile 7 to the carbonyl oxygen of Ser 214 increases from 3.0 Å in the structure of the acyl−enzyme complex to 3.3 Å in the tetrahedral intermediate.
www.nature.com /cgi-taf/DynaPage.taf?file=/nsmb/journal/v8/n8/full/nsb0801_689.html   (3866 words)

  
 Amide hydrolysis -- Facts, Info, and Encyclopedia article   (Site not responding. Last check: 2007-10-14)
Amide hydrolysis involves the C-N bond being broken in reaction with water ((A chemical reaction in which water reacts with a compound to produce other compounds; involves the splitting of a bond and the addition of the hydrogen cation and the hydroxide anion from the water) hydrolysis).
The (Any organic compound containing the group -CONH2) amide is heated under reflux with moderately concentrated acqueous acid or alkali.
If a (A mixture of soluble salts found in arid soils and some bodies of water; detrimental to agriculture) alkali is used, the (An organic acid characterized by one or more carboxyl groups) carboxylic acid loses an H
www.absoluteastronomy.com /encyclopedia/a/am/amide_hydrolysis.htm   (147 words)

  
 mclect3
The acid hydrolysis mechanism involves preliminary protonation of the carbonyl group by an H+ to produce a delocalized cation in the intermediate step.
Es is defined as the difference between the logarithm of the relative rate of acid-catalyzed hydrolysis of a [substituted] carboxy methyl ester and the log of the rate of hydrolysis of methyl acetate (standard).
The rate of hydrolysis for both acid and base-promoted reactions was studied and the realtive rates compared to achieve the Es values.
www.umt.edu /medchem/teaching/421lect8.htm   (582 words)

  
 [No title]
Properties of amines and amides: The amines are similar in structure to the alcohols.
Amides are like ester in their physical properties.
Hydrolysis breaks the amine into its component acid and amine with the addition of one molecule of water.
www.siue.edu /~jshen/CH120/CH120CH15.doc   (1451 words)

  
 Hydrolysis Calculations   (Site not responding. Last check: 2007-10-14)
Theoretical Studies of the ATP Hydrolysis Mechanism of Myosin -- Okimoto et al.
Synthesis, hydrolysis reactions and conformational study of 2-substituted 3,5-di...
Nonenzymatic and enzymatic hydrolysis of alkyl halides: A theoretical study of t...
www.scienceoxygen.com /chem/59.html   (326 words)

  
 Expedient routes to 4,4-dialkyl- 5-methylene-1,3-oxazolines   (Site not responding. Last check: 2007-10-14)
C, non-catalyzed hydration of the amide 3b to 2-methyl-3-oxo-2-butylacetamide 8 occurs in 59% yield (autoclave, 1 h).
The amides 3 represent protected acetylenic amines of the type 11, which are of particular interest for the synthesis of pharmacologically active compounds.
In the aminolysis of amide 3b with ethanolamine, dibutylamine, dioctylamine, morpholine, aniline (50–100°C, 0.5–7 h), as well as in hydrazinolysis (60°C, 3 h) and in hydroxylaminolysis (80°C, 3 h), the initial amide 3b was recovered, and trace amounts (1–2%) of alkynol 1a were sometimes detected.
www.arkat-usa.org /ark/journal/2003/I13_Trofimov/BT-746H/BT-746H.asp   (2427 words)

  
 World Intellectual Property Organization   (Site not responding. Last check: 2007-10-14)
The peptide phosphinothioester is then reacted with the azido peptide accompanied by hydrolysis and loss of nitrogen to generate an amide bond ligating the two peptides.
Hydrolysis of the amidophosphonium salt produces an amide and a phosphine oxide.
Hydrolysis may also be facilitated in appropriate cases by addition of base to the reaction mixture.
www.wipo.int /ipdl/IPDL-CIMAGES/view/pct/getbykey5?KEY=01/87920.011122&ELEMENT_SET=DECL   (8983 words)

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