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Spillane, WJ,Malaubier, JB
2010
April
Tetrahedron Letters
Mechanism of the hydrolysis of the sulfamate EMATE-an irreversible steroid sulfatase inhibitor
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Optional Fields
ESTERS INACTIVATION AMINOLYSIS
51
2059
2062
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 pK(a)s, solvent-reactivity, kinetic isotope effects and determination of activation data reveal that in the pH range from similar to 1 to similar to 8 an S(N)2 (S) solvolytic mechanism is followed and after the pK(a) of EMATE (pK(a) similar to 9) is passed, a second pathway showing a first-order dependence on base operates and an E1cB mechanism is supported. (C) 2010 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tetlet.2010.02.065
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