7377-03-9Relevant articles and documents
Influence of octanohydroxamic acid on the association behavior of cationic surfactants: Hydrolytic cleavage of phosphate ester
Satnami, Manmohan L.,Dewangan, Hitesh K.,Kandpal, Neha,Nagwanshi, Rekha,Ghosh, Kallol K.
, p. 805 - 814 (2016)
The surface properties and mixed micellization behavior of cetyltrimethylammonium bromide (CTAB), tetradecyltrimethylammonium bromide (TTAB) and dodecyltrimethylammonium bromide (DTAB) with octanohydroxamic acid (OHA) have been investigated by means of conductivity and surface tension measurements in aqueous solution and borate buffer at 300 K. The critical micelle concentration (cmc), surface properties such as maximum surface access (Γmax), surface pressure at the cmc (Πcmc) and minimum surface area per molecule (Amin) has been determined. The standard Gibbs free energy of micellization (ΔGm0), standard Gibbs free energy of adsorption (ΔGad0), and standard Gibbs free energy of micellization per alkyl chain (ΔGm,tail0) of cationic surfactant with OHA have been evaluated. The fluorescence quenching technique was used to estimate the aggregation number (Nagg) and packing parameter (P) for determining the structural feature of cationic surfactants in the presence of octanohydroxamic acid. The hydrolytic reaction of paraoxon with octanohydroxamic acid was studied under a cationic micellar system by using OHA- at 9.2 pH and 300 K. The variations of surface properties from aqueous medium to the reaction condition have also been discussed. Pseudophase model (PPM) has been fitted for the quantitative treatment of the data.
Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
F?hrmann, Jan,Hilt, Gerhard
supporting information, p. 20313 - 20317 (2021/08/12)
The acyl nitroso Diels–Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro-induced decomposition could be suppressed in favour of the 1,2-oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3-dienes and hydroxamic acids, giving up to 96 % isolated yield.
Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
Zhu, Mengyi,Wang, Lijuan,He, Jing
supporting information, p. 2030 - 2035 (2020/11/30)
Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.