Development of Porous Ceramic-Immobilized Lipase Catalyst and Optically Active Fluorinated supramolecules

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(1) Development of highly effective and enantioselective catalysis system with immobilized lipase at very low temperatures.(a) For development of an immobilized lipase, we searched the organic bridges coated on porous ceramic support. The organic bridges were combined with porous ceramic by, covalent bonding. When the organic bridge containing isobutyric acid ester moiety was used for the lipase-catalyzed resolution of racemic alcohols, both of enantioselectivity and catalytic activity of the immobilized lipase were much enhanced at -30℃.(b) For further improvement of efficiency of the immobilized lipase, we optimized the acylating agents. When vinyl butanoate was used as the acylating agent, both of the enantioselectivity and the catalytic activity were maximized at -40℃.(2) Development of the optically active fluorinated amines and their application to supramolecular materials.(a) An enantiomerically pure cyanohydrine containing pentafluorophenyl group was obtained by using lipase-catalyzed, resolution. The novel enantiomerically pure 1,2-aminoalcohol containing pentafluorophenyl and phenyl group was synthesized from the chiral cyanohydrine. The X-ray analysis of the compound indicated existence of the interaction between pentafluorophenyl group and alcoholic oxygen atom. The interaction afforded new and useful informations for designing supramolecular materials.(b) The novel enantiomerically pure 1,2-diamine containing pentafluorophenyl groups was synthesized via imino-pinacol coupling reaction. The basicity of the diamine was reduced as compared with the non-fluorinated derivative due to the strong electron-withdrawing ability of the pentafluorophenyl groups. The facts showed the influence of the pentafluorophenyl groups for the nitrogen atom.