Edwards, David R. published the artcileCatalytic Proficiency: The Extreme Case of S-O Cleaving Sulfatases, Application of Potassium 4-nitrophenyl sulfate, the publication is Journal of the American Chemical Society (2012), 134(1), 525-531, database is CAplus and MEDLINE.
As benchmarks for judging the catalytic power of sulfate monoesterases, we sought to determine the rates of spontaneous hydrolysis of unactivated alkyl sulfate monoesters by S-O bond cleavage. Neopentyl sulfate proved to be unsuitable for this purpose, since it was found to undergo hydrolysis by a C-O bond cleaving mechanism with rearrangement of its carbon skeleton. Instead, we examined the temperature dependence of the spontaneous hydrolyzes of aryl sulfate monoesters, which proceed by S-O cleavage. Extrapolation of a Bronsted plot [log(k25N) = (-1.81 ± 0.09) pKaLG + (3.6 ± 0.7)] based on the rate constants at 25 °C for hydrolysis of a series of sulfate monoesters to a pKaLG value of 16.1, typical of an aliphatic alc., yields k25N = 3 × 10-26 s-1. Comparison of that value with established kcat values of bacterial sulfatases indicates that these enzymes produce rate enhancements (kcat/kuncat) of up to 2 × 1026-fold for the hydrolysis of sulfate monoesters. These rate enhancements surpass by several orders of magnitude the ∼1021-fold rate enhancements that are generated by phosphohydrolases, the most powerful biol. catalysts previously known. The hydrolytic rates of phosphate and sulfate monoesters are compared directly, and the misleading impression that the two classes of ester are of similar reactivity is dispelled.
Journal of the American Chemical Society published new progress about 6217-68-1. 6217-68-1 belongs to esters-buliding-blocks, auxiliary class Salt,Nitro Compound,Sulfonate,Benzene, name is Potassium 4-nitrophenyl sulfate, and the molecular formula is C6H4KNO6S, Application of Potassium 4-nitrophenyl sulfate.
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