FUNCTIONAL ORGANIC GELS - FORMATION OF CHIRAL GELS FROM L-GLUTAMIC ACID-DERIVED LIPIDS AND THEIR CHIRAL RECOGNITION ABILITY

被引：8

作者：

IHARA, H ^{[1
]}

SHUDO, K ^{[1
]}

TAKAFUJI, M ^{[1
]}

HIRAYAMA, C ^{[1
]}

HACHISAKO, H ^{[1
]}

YAMADA, K ^{[1
]}

机构：

[1] KUMAMOTO INST TECHNOL,DEPT IND CHEM,IKEDA 860,KUMAMOTO,JAPAN

来源：

KOBUNSHI RONBUNSHU | 1995年 / 52卷 / 10期

关键词：

LIPID MEMBRANES; ORGANIC GELS; FIBROUS AGGREGATES; GLUTAMIC ACID; DIFFERENTIAL SCANNING CALORIMETRY; CIRCULAR DICHROISM; CHIRALITY INDUCTION; ENANTIOSELECTIVITY; PHASE TRANSITION; PHOTOINDUCED POLYMERIZATION;

D O I：

10.1295/koron.52.606

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

L-Glutamic acid-derived lipids having two long-chain alkyl groups and a head group through amide bondings showed gel formation in benzene or ethanol solutions. Electron microscopy, differential scanning calorimetry, and CD spectroscopy indicated that the organic gel formation was induced by the formation of highly-oriented structures like aqueous lipid membranes and the developed microfibrous aggregates. No similar gel formation was observed in the corresponding L-glutamic acid-derived lipids with ester bondings. IR spectroscopy and CAChe-Mechanics and -MOPAC calculations demonstrate that the three amide bondings are effectively used for intermolecular hydrogen bonding aggregation. The resulting organic gels showed chiral induction ability and enantioselective elution behavior for phenylalanine derivatives.

引用

页码：606 / 614

页数：9

共 18 条

[1] CHIRALLY ARRANGED MONOMERIC DYES ON HELICAL BILAYER-MEMBRANES [J].

HACHISAKO, H ;

IHARA, H ;

HIRAYAMA, C ;

YAMADA, K .

LIQUID CRYSTALS, 1993, 13 (02) :307-311

[2]

HIRAYAMA C, 1992, CHROMATOGRAPHIA, V33, P413

[3] LIPID-MEMBRANE ANALOGS - FORMATION OF HIGHLY-ORIENTED STRUCTURES AND THEIR PHASE-SEPARATION BEHAVIOR IN BENZENE [J].

IHARA, H ;

HACHISAKO, H ;

HIRAYAMA, C ;

YAMADA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1244-1245

[4] AMPHIPHILES WITH POLYPEPTIDE-HEAD GROUPS .5. SPECIFIC BINDINGS OF METHYL-ORANGE TO CHIRAL BILAYER-MEMBRANES WITH BETA-ALANYL-L-GLUTAMOYL HEAD GROUPS [J].

IHARA, H ;

HACHISAKO, H ;

HIRAYAMA, C ;

YAMADA, K .

LIQUID CRYSTALS, 1987, 2 (02) :215-221

[5] EFFECT OF PHOTOPOLYMERIZATION ON THE MORPHOLOGY OF HELICAL SUPRAMOLECULAR ASSEMBLIES [J].

IHARA, H ;

TAKAFUJI, M ;

HIRAYAMA, C ;

OBRIEN, DF .

LANGMUIR, 1992, 8 (06) :1548-1553

[6] SELF-ORGANIZATION OF SOLVOPHOBIC, DOUBLE-CHAINED FLUOROCARBON DERIVATIVES IN ORGANIC MEDIA [J].

ISHIKAWA, Y ;

KUWAHARA, H ;

KUNITAKE, T .

CHEMISTRY LETTERS, 1989, (10) :1737-1740

[7] SELF-ASSEMBLY OF BILAYER-MEMBRANES IN ORGANIC-SOLVENTS BY NOVEL AMPHIPHILIC COMPOUNDS [J].

ISHIKAWA, Y ;

KUWAHARA, H ;

KUNITAKE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8530-8531

[8] ENVIRONMENTAL EFFECTS ON VIBRONIC BAND INTENSITIES IN PYRENE MONOMER FLUORESCENCE AND THEIR APPLICATION IN STUDIES OF MICELLAR SYSTEMS [J].

KALYANASUNDARAM, K ;

THOMAS, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) :2039-2044

[9] UNIQUE PROPERTIES OF CHROMOPHORE-CONTAINING BILAYER AGGREGATES - ENHANCED CHIRALITY AND PHOTOCHEMICALLY INDUCED MORPHOLOGICAL CHANGE [J].

KUNITAKE, T ;

NAKASHIMA, N ;

SHIMOMURA, M ;

OKAHATA, Y ;

KANO, K ;

OGAWA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6642-6644

[10] ENHANCED CIRCULAR-DICHROISM AND FLUIDITY OF DISK-LIKE AGGREGATES OF A CHIRAL, SINGLE-CHAIN AMPHIPHILE [J].

KUNITAKE, T ;

NAKASHIMA, N ;

MORIMITSU, K .

CHEMISTRY LETTERS, 1980, (11) :1347-1350

← 1 2 →