2308-54-5Relevant articles and documents
Efficient conversion to Cypridina luciferin from Cypridina luciferyl sulfate, coupled with enzymatic sulfation of acetic acid
Nakamura, Mitsuhiro,Matsuda, Kazuo,Morikawa, Takashi,Ishizuka, Kohsuke,Inouye, Satoshi
, p. 678 - 684 (2020)
In Cypridina (Vargula) hilgendorfii, Cypridina luciferin is converted from Cypridina luciferyl sulfate by a sulfotransferase with adenosine 3′, 5′-diphosphate (PAP), and is used for the luminescence reaction of Cypridina luciferase. We found that the luminescence activity of crude extracts of C. hilgendorfii was significantly stimulated by the addition of acetic acid. This stimulation may be explained by an efficient supply of PAP from 3′-phosphoadenosine 5′-phosphosulfate (PAPS) catalyzed by a sulfotransferase. Thus, acetic acid acts as a sulfate acceptor from PAPS, followed by forming acetyl sulfate and PAP. The structure of acetyl sulfate was identified using mass spectrometry and it spontaneously decomposed to acetic acid and free sulfate ion in aqueous solutions. This enzymatic conversion from Cypridina luciferyl sulfate to Cypridina luciferin could be coupled with acetic acid and PAPS by a sulfotransferase.
Synthesis of mixed acid anhydrides from methane and carbon dioxide in acid solvents
Zerella, Mark,Mukhopadhyay, Sudip,Bell, Alexis T.
, p. 3193 - 3196 (2003)
(Matrix presented) The reaction of CH4 with CO2 has been performed in anhydrous acids using VO(acac)2 and K 2S2O8 as promoters. NMR analysis establishes that the primary product is a mixed anhydride of acetic acid and the acid solvent. In sulfuric acid, the overall reaction is CH4 + CO 2 + SO3 → CH3C(O)-O-SO3H. Hydrolysis of the mixed anhydride produces acetic acid and the solvent acid. When trifluoroacetic acid is the solvent, acetic acid is primarily formed via the reaction CH4 + CF3COOH → CH3COOH + CHF3.
Synthesis and proton conductivity of partially sulfonated poly([vinylidene difluoride-co-hexafluoropropylene]-b-styrene) block copolymers
Shi, Zhiqing,Holdcroft, Steven
, p. 4193 - 4201 (2005)
A series of novel, amphiphilic block copolymers comprising of sulfonated poly([vinylidene difluoride-co-hexafluoropropylene]-b-styrene) [P(VDF-co-HFP)-b-SPS] were synthesized. The number-average molecular weights of the fluorous and polystyrene segments were 17 900 and 8100 g/mol, respectively. Sulfonation of the polystyrene segment to different extents provided a series of polymers which were cast into films to yield proton exchange membranes with varying ion exchange capacity (IEC). Proton conductivity of the membranes increased significantly when the IEC was increased from 0.5 to 1.2 mmol/g. For 0.9-1.2 mmol/g IEC membranes, the conductivity was similar to Nafion 117, significantly higher than random copolymers of polystyrene and sulfonated polystyrene, and twice that of nonfluorous block copolymer membranes based on sulfonated poly(styrene-b-[ethylene-co-butylene]-b-styrene) (S-SEBS) and sulfonated hydrogenated poly(butadiene-b-styrene) (S-HPBS) copolymers. TEM revealed a disruption in ordered morphology with increasing degree of sulfonation. Morphological structures of membranes having 0.6-1.2 mmol/g IEC comprised of interconnected networks of ion channels, each of 8-15 nm width.
Polymer-supported sulfonated magnetic resin: An efficient reagent for esterification of O-alkyl alkylphosphonic-and carboxylic-acids
Purohit, Ajay Kumar,Kumar, Ajeet,Singh, Varoon,Goud D, Raghavender,Jain, Rajiv,Dubey
supporting information, p. 6844 - 6846 (2015/01/09)
A mild and efficient synthetic method has been developed for the esterification of O-alkyl alkylphosphonic-and carboxylic-acids using polymer-supported sulfonated magnetic resins. Polymer-supported resins are recovered using an external magnet and reused several times.
Experimental and molecular modelling studies on aromatic sulfonation
Morley, John O.,Roberts, David W.,Watson, Simon P.
, p. 538 - 544 (2007/10/03)
The mechanism of the sulfonation of toluene has been explored both experimentally and theoretically using molecular orbital methods. Sulfonation with sulfur trioxide is proposed to proceed initially via the formation of a toluene-S2O6 π-complex (3) which rearranges to form a Wheland pyrosulfonate intermediate (5) which in turn undergoes a facile prototropic rearrangement involving the transfer of the ring hydrogen at the sp3 carbon to the sulfonate oxygen atom to form toluenepyrosulfonic acid (7). Once formed, this acid is thought to attack toluene to form two equivalents of toluenesulfonic acid (6) which preferentially react with sulfur trioxide to re-form the pyrosulfonic acid (7). Experimentally, sulfonation using either acetylsulfonic acid (9), trifluoroacetylsulfonic acid (10), or trimethylacetylsulfonic acid (11), as models for pyrosulfonic acid (7), appears to show second order kinetics at room temperature. The reaction with acetylsulfonic acid (9) shows no significant kinetic isotope effect when 4deuterotoluene is used as the substrate, suggesting that sulfonation proceeds via attack of the π-electrons of the toluene ring at the sulfur atom, S8, of acetylsulfonic acid or toluenepyrosulfonic acid with simultaneous cleavage of the O7-S8 bond, where the displaced acetate or toluenesulfonate anion respectively can facilitate the removal of the ring proton at the sp3 carbon.
Method of sulfation
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, (2008/06/13)
A method for sulfating a hydroxy amino acid or a residue of such an amino acid in a peptide by reaction with a reagent which is a tertiaryammonium salt of acetylsulfuric acid having the formula: wherein R is triethylamine, ethyldiisopropylamine, pyridine, 4-methylmorpholine or 4-N,N-dimethylaminopyridine. The α-amino group and any other labile side chains present may be protected or may be left unprotected at the time the sulfation takes place.
Monoacyl Sulfates as Intermediates for α-Halogenation of Aliphatic Acids
Ogata, Yoshiro,Adachi, Koichi
, p. 1182 - 1184 (2007/10/02)
The mechanism of the α-halogenation of aliphatic carboxylic acids, promoted by ClSO3H or oleum, has been reexamined.Ketenes, which have been postulated as the intermediates in this halogenation, have been found to react with I2 much faster than a mixture of the corresponding acid and ClSO3H.Evidence is presented to support the hypothesis that the halogenation proceeds through the cyclic enol form of the monoacyl sulfate RR'CHCO2SO3H (3) rather than through the ketene.
