4112-03-2Relevant articles and documents
Proton-in-flight mechanism for the spontaneous hydrolysis of N-methyl O-phenyl sulfamate: Implications for the design of steroid sulfatase inhibitors
Edwards, David R.,Wolfenden, Richard
experimental part, p. 4450 - 4453 (2012/06/30)
The hydrolysis of N-methyl O-phenyl sulfamate (1) has been studied as a model for steroid sulfatase inhibitors such as Coumate, 667 Coumate, and EMATE. At neutral pH, simulating physiological conditions, hydrolysis of 1 involves an intramolecular proton transfer from nitrogen to the bridging oxygen atom of the leaving group. Remarkably, this proton transfer is estimated to accelerate the decomposition of 1 by a factor of 1011. Examination of existing kinetic data reveals that the sulfatase PaAstA catalyzes the hydrolysis of sulfamate esters with catalytic rate accelerations of ～104, whereas the catalytic rate acceleration generated by the enzyme for its cognate substrate is on the order of ～1015. Rate constants for hydrolysis of a wide range of sulfuryl esters, ArOSO2X-, are shown to be correlated by a two-parameter equation based on pKa ArOH and pKaArOSO2XH.
SYNTHESIS OF METHYLSULFAMIDIC ACID.
Gareev,Bol'shedvorskaya,Cherkashina,Flippova,Gaer,Vereshchagin,Sakovich
, p. 1013 - 1016 (2007/10/02)
Methylsulfamidic acid (MSA) and its homologs are key substances in production of synthetic sweeteners, dyes, and means of control of agricultural pests. A method has been devised for production of MSA by sulfonation of dimethylurea with 20-30% oleum in absence of a solvent by 75-80 degree , followed by isolation of MSA by crystallization in 70-75% sulfuric acid. The dependence of the MSA yield on different reaction conditions was studied. Three reaction routes studied were: sulfonation with sulfur trioxide, sulfonation with oleum in a solvent, and sulfonation with oleum without a solvent.
