High stereoselectivity in the deacylation of p-nitrophenyl N-acylphenylalanates by bilayer vesicular systems which include dipeptide-type nucleophiles
Abstract
The deacylation of p-nitrophenyl N-acylphenylalanated with bilayer vesicular systems comprising dipeptide-type nucleophiles and a cationic double chain surfactant resulted in high stereoselectivity (kcatL/kcatD= 29.6 at 25 °C and 83.6 at 10 °C) for the deacylation of p-nitrophenyl N-dodecanoylphenylalanate by the catalytic system of N-(N-benzyloxycarbonyl-L-leucyl)-L-histidine and N,N-didodecyl-N,N-dimethylammonium bromide.