人工脂質膜における不斉加水分解制御 : 不飽和脂肪酸及びミセルの効果

概要

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The stereoselective hydrolysis of the long-chained substrate (p-nitrophenyl N-dodecanoyl-D (L) -phenylalaninate, D (L) -S12) has been found to be controlled by addition of unsaturated fatty acids or micelles in the artificial membrane systems. The noteworthy aspects are as follows : (a) Methyl oleate enhanced the catalytic efficiency (reflected in the second-order rate constant, ka, obsd) for the hydrolysis of D(L)-S12 in the catalytic system of N-benzyloxycarbonyl-L-phenylalanyl-L-histidyl-L-leucine (Z-PheHisLeu) and ditetradecyldimethylammonium bromide (2 C14Br) along with the elevation of phase transition temperature. On the other hand, (b)γ-irradiated methyl linoleate reduced the catalytic efficiency of Z-PheHisLeu with time course. This would be attributed to the autoxidation of γ-irradiated methyl linoleate; (c) the high enantioselectivity (kLaobsd/kDaobsd =28) of S12 with Z-PheHisLeu in the membrane system of 2 C14 Br (1mM) was elevated dramatically by addition of micelles (hexadecylbenzyldimethylammonium chloride, 7 mM) and attained to enantiomer rate ratio (kLaobsd/kDaobsd =67) at room temperature.
社団法人日本油化学会の論文