TY - JOUR
T1 - Synthesis, reactivity and applications of 1-fluoroalkyl carboxylates: novel synthetic substrates for esterases and lipases
AU - Rye, Carl S
AU - Baell, Jonathan Bayldon
AU - Street, Ian Philip
PY - 2007
Y1 - 2007
N2 - A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.
AB - A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.
UR - http://www.sciencedirect.com/science/article/pii/S0040402007002700
U2 - 10.1016/j.tet.2007.02.059
DO - 10.1016/j.tet.2007.02.059
M3 - Article
VL - 63
SP - 3306
EP - 3311
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 16
ER -