Fluid and chiral ephedrinium myristate micellar fibers

被引：31

作者：

Trager, O ^{[1
]}

Sowade, S ^{[1
]}

Bottcher, C ^{[1
]}

Fuhrhop, JH ^{[1
]}

机构：

[1] FREE UNIV BERLIN,INST ORGAN CHEM,D-14195 BERLIN,GERMANY

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1997年 / 119卷 / 39期

关键词：

D O I：

10.1021/ja971803y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Myristic acid crystallizes as 1:1 mixture with its sodium salt (acid soap) at pH 9.8, as pure sodium salt (soap) upon addition of sodium chloride and gives long fibers (curds) of a carboxylate monohydrate at pH 11.5. Transmission electron microscopy shows micellar fibers as structural units of the curds. Curvature of the myristate bilayer is enforced by hydration, not by repulsive forces between anions. Ephedrinium and pseudoephedrinium myristate produce stable isolated fibers of bimolecular thickness in water. They dissolve magnesium octaethylporphyrin in a chiral arrangement and show strong CD effects. The aqueous solution is viscoelastic. Twisted ribbons were obtained from the cationic analogue cetyltrimethylammonium with the chiral adenosine monophosphate counterion.

引用

页码：9120 / 9124

页数：5

共 23 条

[1] IONIZATION AND PHASE-BEHAVIOR OF FATTY-ACIDS IN WATER - APPLICATION OF THE GIBBS PHASE RULE [J].

CISTOLA, DP ;

HAMILTON, JA ;

JACKSON, D ;

SMALL, DM .

BIOCHEMISTRY, 1988, 27 (06) :1881-1888

[2] ON MICELLE FORMATION AND PHASE-SEPARATION [J].

CISTOLA, DP ;

SMALL, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3214-3215

[3] VISCOELASTIC MICELLAR SOLUTIONS - MICROSCOPY AND RHEOLOGY [J].

CLAUSEN, TM ;

VINSON, PK ;

MINTER, JR ;

DAVIS, HT ;

TALMON, Y ;

MILLER, WG .

JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (01) :474-484

[4] THE CHIRAL BILAYER EFFECT STABILIZES MICELLAR FIBERS [J].

FUHRHOP, JH ;

SCHNIEDER, P ;

ROSENBERG, J ;

BOEKEMA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3387-3390

[5] CHIRAL MICELLAR PORPHYRIN FIBERS WITH 2-AMINOGLYCOSAMIDE HEAD GROUPS [J].

FUHRHOP, JH ;

DEMOULIN, C ;

BOETTCHER, C ;

KONING, J ;

SIGGEL, U .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4159-4165

[6] LONG-LIVED MICELLAR N-ALKYLALDONAMIDE FIBER GELS - SOLID-STATE NMR AND ELECTRON-MICROSCOPIC STUDIES [J].

FUHRHOP, JH ;

SVENSON, S ;

BOETTCHER, C ;

ROSSLER, E ;

VIETH, HM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4307-4312

[7] MICELLAR RODS AND VESICULAR TUBULES MADE OF 14''',16'''-DIAMINOPORPHYRINS [J].

FUHRHOP, JH ;

BINDIG, U ;

SIGGEL, U .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11036-11037

[8]

FUHRHOP JH, 1974, ANGEW CHEM, V86, P363

[9] RESOLUTION OF (+/-)-2-TETRADECYLOXIRANECARBOXYLIC ACID - ABSOLUTE-CONFIGURATION AND CHIRAL SYNTHESIS OF THE HYPOGLYCEMIC R ENANTIOMER AND BIOLOGICAL-ACTIVITY OF ENANTIOMERS [J].

HO, W ;

TARHAN, O ;

KIORPES, TC ;

TUTWILER, GF ;

MOHRBACHER, RJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (06) :1094-1097

[10]

Hoffman H., 1988, ANGEW CHEM, V100, P933, DOI DOI 10.1002/ANGE.19881000707

← 1 2 3 →