Syntheses of (Z)-and (E)-4-amino-2-(trifluoromethyl)-2-butenoic acid and Their inactivation of γ-aminobutyric acid aminotransferase

TR Johnson, RB Silverman

Index: Johnson, Theodore R.; Silverman, Richard B. Bioorganic and Medicinal Chemistry, 1999 , vol. 7, # 8 p. 1625 - 1636

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Citation Number: 19

Abstract

(Z)-and (E)-4-amino-2-(trifluoromethyl)-2-butenoic acid (4 and 5, respectively) were synthesized and investigated as potential mechanism-based inactivators of γ-aminobutyric acid aminotransferase (GABA-AT) in a continuing effort to map the active site of this enzyme. The core α-trifluoromethyl-α, β-unsaturated ester moiety was prepared via a Reformatsky/reductive elimination coupling of the key intermediates tert-butyl 2, 2-dichloro ...