Enantioselective Hydrolysis of Amino Acid Esters by Liquid-Surfactant Membrane Including the Active Tripeptide

Abstract

The enantioselective hydrolysis of a long-chain substrate (p-nitrophenyl N-dodecanoyl-D (L) -phenylalaninate, D (L) -S₁₂) was carried out in hybrid assemblies (liquidsurfactant membrane) composed of 59 mol % vesicular (ditetradecyldimethylammonium bromide, 2C₁₄Br) and 41 mol% micellar (hexadecyltrimethylammonium bromide, CTAB) surfactants.
High enantioselectivity (k^L_ψ/k^D_ψ=35) was obtained for the hydrolysis of D (L) -S₁₂ with the active tripeptide (N- (benzyloxycarbonyl) -L-phenylalanyl-L-histidyl-L-leucine, Z-PheHisLeu) at the phase transition temperature (15°C) of the hybrid assemblies of 2C₁₄Br and CTAB, which was kept stable as spherical large vesicles with a radius of 110-115 nm for at least one week.