Mechanism of the hydrolysis of the sulfamate EMATE—an irreversible steroid sulfatase inhibitor |
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| Authors: | William J Spillane Jean-Baptiste Malaubier |
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| Institution: | School of Chemistry, National University of Ireland, Galway, Ireland |
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| Abstract: | The kinetics of hydrolysis of the medicinally important sulfamate ester EMATE have been probed over a wide pH range and into moderately strong base (H_ region). Analysis of the pH/H_-rate profile, measurements of pKas, solvent-reactivity, kinetic isotope effects and determination of activation data reveal that in the pH range from ∼1 to ∼8 an SN2 (S) solvolytic mechanism is followed and after the pKa of EMATE (pKa ∼9) is passed, a second pathway showing a first-order dependence on base operates and an E1cB mechanism is supported. |
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