Mechanism of the hydrolysis of the sulfamate EMATE—an irreversible steroid sulfatase inhibitor

Autor:	Jean-Baptiste Malaubier, William J. Spillane
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Base (chemistry) Second pathway Stereochemistry Organic Chemistry Kinetics Biochemistry Hydrolysis chemistry Drug Discovery Kinetic isotope effect Steroid sulfatase Ph range E1cB-elimination reaction
Zdroj:	Tetrahedron Letters. 51:2059-2062
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2010.02.065
Popis:	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 p K a s, solvent-reactivity, kinetic isotope effects and determination of activation data reveal that in the pH range from ∼1 to ∼8 an S N 2 ( S ) solvolytic mechanism is followed and after the p K a of EMATE (p K a ∼9) is passed, a second pathway showing a first-order dependence on base operates and an E1cB mechanism is supported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a02eaa4912e2db7c05636e254a93c901 https://doi.org/10.1016/j.tetlet.2010.02.065 Zobrazit plný text záznamu Full Text from ScienceDirect