74-81-7Relevant articles and documents
Micellization and catalytic properties of cationic surfactants with head groups functionalized with a hydroxyalkyl fragment
Mirgorodskaya, Alla B.,Yackevich, Ekaterina I.,Syakaev, Victor V.,Zakharova, Lucia Ya.,Latypov, Shamil K.,Konovalov, Alexander I.
, p. 3153 - 3163 (2013/01/15)
The catalytic activity of two homological series of cationic surfactants bearing a hydroxyalkyl fragment in the head groups R(CH3)2N+(CH2CH2OH)Br-and R(CH3)2N+/s
Development of a lipase-based optical assay for detection of DNA
Pinijsuwan, Suttiporn,Shipovskov, Stepan,Surareungchai, Werasak,Ferapontova, Elena E.,Gothelf, Kurt V.
experimental part, p. 6352 - 6356 (2011/10/10)
A lipase-based assay for detection of specific DNA sequences has been developed. Lipase from Candida antarctica was conjugated to DNA and captured on magnetic beads in a sandwich assay, in which the binding was dependent on the presence of a specific target DNA. For amplification and to generate a detectable readout the captured lipase was applied to an optical assay that takes advantage of the enzymatic activity of lipase. The assay applies p-nitrophenol octanoate (NPO) as the substrate and in the presence of lipase the ester is hydrolyzed to p-nitrophenolate which has a strong absorbance at 405 nm. The method provides detection a detection limit of 200 fmol target DNA and it was able to distinguish single base mismatches from the fully complementary target.
Nucleophilic substitution in carboxylic esters in oil-in-water microemulsions
Mirgorodskaya,Kudryavtseva
, p. 1261 - 1265 (2007/10/03)
In hydrolysis and aminolysis of p-nitrophenyl esters of carboxylic acids in oil-in-water microemulsions on the basis of surfactants of various nature, a complex mechanism of the effect of the medium is operative, including shift of acid-base equilibria in the nucleophile. The rate constants of the processes studied are quantitatively related to the surface potential of the microdroplet. Varied hydrophobicity of the nucleophile and substrate changes the site of the reaction act and the relative contributions of aminolysis and hydrolysis.
The Kinetics of Basic Cleavage of Nitrophenyl Alkanoate Esters by 'Hydroxypropyl-β-cyclodextrin' in Aqueous Solution
Gadosy, Timothy A.,Tee, Oswald S.
, p. 715 - 722 (2007/10/02)
The kinetics of cleavage of m- and p-nitrophenyl alakanoates by 'hydroxypropyl-β-cyclodextrin' (Hp-β-CD) in basic aqueous solution vary significantly with the chain length of the esters (C2 to C10).For both series of esters with short chains (C2 to C6) simple saturation kinetics are observed, indicative of 1:1 (ester:CD) binding and reaction of one molecule of ester with one molecule of Hp-β-CD.For longer chains, there is also a cleavage process involving two molecules of Hp-β-CD.This type of behaviour was not found previously for the same esters reacting with α-CD and with β-CD but it has been observed for some carboxynitrophenyl alkanoates.With the longest esters there is also evidence of productive 1:2 (ester:CD) binding.For the 1:1 binding, there is a linear dependence of the strength on acyl chain length and the close similarity of the dissociation constants for the two series of esters implicate inclusion of the alkyl chains of the esters acyl groups.Transition-state binding is more complex: for the meta-nitro isomers aryl-group inclusion appears dominant whereas for the para isomers there seems to be a switch from aryl-group inclusion to acyl-group inclusion, occurring at a chain length of C6-C7.
Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations
Wiberg, Kenneth B.,Waldron, Roy F.
, p. 7697 - 7705 (2007/10/02)
The enthalpies of hydrolysis of the monocyclic lactones from γ-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl having the number of atoms were studied in the fashion. The enthalpies of reduction of the lactones to the corresponding α,ω-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the of γ-butyrolactone and δ-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of γ-butyrolactone and δ-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.
Contrasting Behaviors in the Cleavage of Aryl Alkanoates by α- and β-Cyclodextrins in Basic Aqueous Solution
Tee, Oswald S.,Du, Xian-xian
, p. 1837 - 1839 (2007/10/02)
The kinetics of ester cleavage of 4-carboxy-2-nitrophenyl alkanoates (C2, C4, C6, C7, C8) in aqueous base containing α- or β-cyclodextrin (α- or β-CD) indicate that for the three longer esters there are processes involving two CD molecules which are quite distinct: with α-CD a 2:1 binding leads to inhibition; with β-CD a second-order process provides catalysis.
