5705-41-9Relevant academic research and scientific papers
Influence of Microheterogeneous Environments of Sodium Dodecyl Sulfate on the Kinetics of Oxidation of l -Serine by Chloro and Chlorohydroxo Complexes of Gold(III)
Maiti, Krishnendu,Sen, Pratik K.,Barik, Anil K.,Pal, Biswajit
, p. 5270 - 5282 (2018)
The oxidation of l-serine by chloro and chlorohydroxo complexes of gold(III) was spectrophotometrically investigated in acidic buffer media in the absence and presence of the anionic surfactant sodium dodecyl sulfate (SDS). The oxidation rate decreases with increase in either [H+] or [Cl-]. Gold(III) complex species react with the zwitterionic form of serine to yield acetaldehyde (principal reaction product) through oxidative decarboxylation and subsequent deamination processes. A reaction pathway involving one electron transfer from serine to Au(III) followed by homolytic cleavage of α-C-C bond with the concomitant formation of iminic cation intermediate has been proposed where Au(III) is initially reduced to Au(II). The surfactant in the submicellar region exhibits a catalytic effect on the reaction rate at [SDS] ≤ 4 mM; however, in the postmicellar region an inhibitory effect was prominent at [SDS] ≥ 4 mM. The catalytic effect below the critical micelle concentration (cmc) may be attributable to the electrostatic attraction between serine and SDS that, in turn, enhances the nucleophilicity of the carboxylate ion of the amino acid. The inhibition effect beyond cmc has been explained by considering the distribution of the reactant species between the aqueous and the micellar pseudophases that restricts the close association of the reactant species. The thermodynamic parameters δH0 and δS0 associated with the binding between serine and SDS micelle were calculated to be -14.4 ± 2 kJ mol-1 and -6.3 ± 0.5 J K-1 mol-1, respectively. Water structure rearrangement and micelle-substrate binding play instrumental roles during the transfer of the reactant species from aqueous to micellar pseudophase.
Defluorination of 4-fluorothreonine by threonine deaminase
Deng, Hai,Wu, Linrui
supporting information, p. 6236 - 6240 (2020/09/07)
4-Fluorothreonine (4-FT) is the only naturally occurring fluorinated amino acid antibiotic. Although two conserved proteins in the 4-FT pathway have been found to be involved in self-detoxification mechanisms, the 4-FT-producing strains may also require an alternative pathway to degrade the intracellular 4-FT. In this study, we examined the possible degradation role of three enzymes involved in threonine metabolite pathways toward 4-FT as a possible degradation route to avoid in vivo 4-FT accumulation. Among these three enzymes, threonine deaminase was found to catalyse a defluorination reaction to generate 4-hydroxy-α-ketobutyrate, which is supposed to be further metabolised by an aldolase that likely is a unique occurrence in the 4-FT-producing strains. Our finding may constitute a 4-FT degradation pathway as a complementary resistance mechanism.
Synthesis of N-Sulfonylformamidines by tert-butyl Hydroperoxide–Promoted, metal-free, direct oxidative dehydrogenation of aliphatic amines
Rouzi, Ayijiamali,Hudabaierdi, Ruzeahong,Wusiman, Abudureheman
supporting information, p. 2475 - 2481 (2018/04/14)
A direct and convenient metal-free method to prepare sulfonyl amidines in the presence of aqueous tert-butyl hydroperoxide (T-HYDRO) has been developed. Different tertiary and secondary amines were tested for compatibility with the oxidative conditions and could be coupled with sulfonyl azides to form the corresponding amidines in moderate to good yields.
Is the tungsten(IV) complex (NEt4)2[WO(mnt)2] a functional analogue of acetylene hydratase?
Schreyer, Matthias,Hintermann, Lukas
supporting information, p. 2332 - 2339 (2017/11/16)
The tungsten(IV) complex (Et4N)2[W(O)(mnt)2] (1; mnt = maleonitriledithiolate) was proposed (Sarkar et al., J. Am. Chem. Soc. 1997, 119, 4315) to be a functional analogue of the active center of the enzyme acetylene hydratase from Pelobacter acetylenicus, which hydrates acetylene (ethyne; 2) to acetaldehyde (ethanal; 3). In the absence of a satisfactory mechanistic proposal for the hydration reaction, we considered the possibility of a metal-vinylidene type activation mode, as it is well established for rutheniumbased alkyne hydration catalysts with anti-Markovnikov regioselectivity. To validate the hypothesis, the regioselectivity of tungsten- catalyzed alkyne hydration of a terminal, higher alkyne had to be determined. However, complex 1 was not a competent catalyst for the hydration of 1-octyne under the conditions tested. Furthermore, we could not observe the earlier reported hydration activity of complex 1 towards acetylene. A critical assessment of, and a possible explanation for the earlier reported results are offered. The title question is answered with "no".
Effect of CHAPS and CPC micelles on Ir(III) catalyzed Ce(IV) oxidation of aliphatic alcohols at room temperature and pressure
Ghosh, Aniruddha,Saha, Rumpa,Saha, Bidyut
, p. 223 - 237 (2014/05/06)
Kinetics of cerium(IV) oxidation of aliphatic alcohols: ethanol, propanol, propan-2-ol, 1-butanol and 2-butanol were studied at 30 °C in the presence and absence of surfactants in acidic medium. The reaction was studied under pseudo-first-order conditions
Kinetics and mechanism of oxidation of glycine and alanine by Oxone? catalyzed by bromide ion
Thombare, Malharrao R.,Gokavi, Gavisiddappa S.
, p. 1545 - 1551 (2015/02/18)
Oxidation of glycine and alanine by Oxone? catalysed by bromide ions has been studied in acidic medium. The reaction is initiated by the oxidation of bromide to bromine, which then reacts with the amino acid. The formation of bromine is supported by the spectrophotometric examination of the reaction mixture. The proposed intermediate involves a complex formation between bromine and the anion of the amino acid. The rate of the reaction is inhibited by an increase in the hydrogen ion concentration due to the protonation equilibria of the amino acids. A mechanism is proposed and the derived rate law was verified graphically. Effect of relative permittivity, ionic strength and temperature was also carried out and these effects are also in support of the mechanism proposed.
Oxidized single-walled carbon nanotubes (swcns-cooh) as a new catalyst for the protection of carbonyl groups as hydrazones
Borazjani, Maryam Kiani,Safaei, Hamid Reza,Panahandeh, Majid,Kiani, Ali Reza,Kiani, Masoumeh,Mofarahi, Masoud
, p. 279 - 281 (2013/12/04)
Nano-materials are considered as suitable heterogeneous catalysts for many organic reactions. Herein oxidized carbon nanotube (SWCNTs-COOH) has been reported as a heterogeneous catalyst, for protection of carbonyl groups as hydrazones in EtOH at 80 C. The reactions proceed smoothly with good to excellent yields, and the SWCNTs-COOH used can be recycled.
Selective reduction of esters to aldehydes under the catalysis of well-defined NHC-iron complexes
Li, Haoquan,Misal Castro, Luis C.,Zheng, Jianxia,Roisnel, Thierry,Dorcet, Vincent,Sortais, Jean-Baptiste,Darcel, Christophe
supporting information, p. 8045 - 8049 (2013/08/23)
On a direct course to the aldehyde: Hydrosilylation catalyzed by a well-defined N-heterocyclic-carbene-iron complex under UV irradiation enabled the selective reduction of esters to aldehydes (see scheme; Bn=benzyl, Mes=mesityl). The low catalyst loading and very mild reaction conditions make this chemoselective transformation a promising alternative to the reduction of esters with diisobutylaluminum hydride. Copyright
Selective reduction of carboxylic acids to aldehydes through manganese catalysed hydrosilylation
Zheng, Jianxia,Chevance, Soizic,Darcel, Christophe,Sortais, Jean-Baptiste
supporting information, p. 10010 - 10012 (2013/10/22)
The direct reduction of carboxylic acids to disilylacetals was achieved through a manganese catalyzed hydrosilylation reaction in the presence of triethylsilane under mild conditions, at r.t. and under UV irradiation (350 nm). The aldehydes were obtained in good to excellent yields after acidic hydrolysis.
Revisiting the reaction of hydroxyl radicals with vicinal diols in water
Jiang, Dong,Barata-Vallejo, Sebastian,Golding, Bernard T.,Ferreri, Carla,Chatgilialoglu, Chryssostomos
supporting information; experimental part, p. 1102 - 1107 (2012/04/04)
The carbonyl products of the reactions of hydroxyl radicals with three vicinal diols (ethane-1,2-diol, propane-1,2-diol and butane-2,3-diol) have been identified and quantified. Hydroxyl radicals were produced by γ-radiolysis of N2O-saturated aqueous solutions. The reactions result in the formation of alkoxyl radicals (~15%) followed by β-fragmentation, and α-hydroxyl alkyl radicals that undergo H2O elimination. The latter process is part of a radical chain reaction at higher diol concentrations.
