Lipid bilayer fibers from diastereomeric and enantiomeric N-octylaldonamides

Fuhrhop, Jürgen‐Hinrich; Schnieder, Peter; Boekema, Egbert J.; Helfrich, W.

doi:10.1021/ja00217a028

Cited by 220 publications

(149 citation statements)

References 3 publications

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“…Remarkably, however, almost all have pitch angles of either 11°o r 54°. Several theoretical models have been proposed to explain the formation and properties of helical ribbons, which sometimes form in complex fluids containing chiral amphiphilic molecules (3)(4)(5)(6)(7)(8)(9)(10). These theories were designed to describe the helical ribbons in solutions containing a single species of phospholipids, which can form bilayers.…”

mentioning

confidence: 99%

Structure of cholesterol helical ribbons and self-assembling biological springs

Khaykovich

Hossain

McManus³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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We report the results of x-ray-scattering studies of individual helical ribbons formed in multicomponent solutions of cholesterol solubilized by various surfactants. The solutions were chemically defined lipid concentrate (CDLC) and model bile. In these and many analogous multicomponent surfactant-cholesterol solutions, helical ribbons of two well defined pitch angles, namely 11°and 54°, are formed. We have suggested previously that this remarkable stability results from an underlying crystalline structure of the sterol ribbon strips. Using a synchrotron x-ray source, we have indeed observed Bragg reflections from individual ribbons having 11°pitch angle. We have been able to deduce the parameters of the unit cell. The crystal structure of these ribbons is similar to that of cholesterol monohydrate, with the important difference that the length of the unit cell perpendicular to the cholesterol layers is tripled. We discuss possible origins for this triplication as well as the connection between the crystalline structure and the geometrical form of the helical ribbons.crystal structure ͉ x-ray diffraction ͉ crystallization ͉ surfactants S elf assembly of helical ribbons in complex fluids is an interesting phenomenon, which poses fundamental questions about the molecular structure, elastic properties, and kinetic evolution of these objects. In particular, quaternary solutions, which contain cholesterol, nonionic surfactants, and lipids, spontaneously form helical ribbons with characteristic pitch angles of 11°and 54°. These helical ribbons are long rectangular strips, which curl along a cylindrical surface. These objects were discovered in human gallbladder bile, where they form spontaneously upon the dilution of bile. This dilution produces a solution supersaturated with respect to cholesterol (1). Formation of similar helical ribbons has been later reported in Ͼ20 different solutions with various sterols analogous to cholesterol, surfactants, and phospholipids or fatty acids (2). These helical ribbons form in a variety of axial lengths, widths, and radii. Remarkably, however, almost all have pitch angles of either 11°o r 54°. Several theoretical models have been proposed to explain the formation and properties of helical ribbons, which sometimes form in complex fluids containing chiral amphiphilic molecules (3-10). These theories were designed to describe the helical ribbons in solutions containing a single species of phospholipids, which can form bilayers. Therefore, the ribbons were modeled theoretically as fluid bilayers, where hydrophobic carbon chains are sandwiched between hydrophilic head groups. Calculations of the properties of such membranes are usually based on the curvature elasticity model (11), which is founded on general physical arguments about the dependence of the fluid membrane elastic free energy on its curvature. Based on this model, subsequent theories attempted to explain the geometrical and elastic properties of the helical ribbons. For example, the formation of helices is attributed to b...

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mentioning

confidence: 99%

Structure of cholesterol helical ribbons and self-assembling biological springs

Khaykovich

Hossain

McManus³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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“…From 1 H-NMR spectroscopy it was found that gelation was induced by the formation of hydrogen bonds. For surfactant 17 the only organic solvent known to be gelated is o-xylene [25]. In these gels long fibers were observed, which consist of multiple concentrically stacked sheets.…”

Section: Figure 4 Amide and Carbohydrate Containing Gelatorsmentioning

confidence: 99%

“…It is clearly seen that the twisted structure observed in the light micrographs is a single turn of the sheets along the long axis of the fiber. Twisting has been observed in other fiber type aggregates, but the mechanism that is responsible for the formation of the twists in the fibers is not clear [25,57]. Most likely the formation of twists is driven by a reduction of the interfacial free energy, in which view a preferred screw sense can be explained by an anisotropy of the interfacial free energy in aggregates of chiral molecules.…”

Section: Figure 14mentioning

confidence: 99%

Low Molecular Weight Gelators for Organic Solvents

Esch

Schoonbeek

Loos

et al. 1999

Supramolecular Science: Where It Is and Where It Is Going

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“…The aggregation behaviour of N-alkyl-hexonamides and subsequent formation of the characteristic ordered structures has recently been described (Pfannemueller & Welte, 1985;Fuhrhop et al, 1988). Such structures were formed by cooling hot micellar aqueous solutions down to temperatures where amide hydrogen bond chains are formed in a co-operative reaction sequence.…”

Section: Introductionmentioning

confidence: 99%

“…lc). The 'screw sense' of the chiral aggregates is specific and correlates with the configuration of the sugar head group (Fuhrhop et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

Assignment of two ultrastructures formed by a mixture of hexonamides using autoradiography and electron microscopy

Boettcher¹,

Boekema²,

Fuhrhop³

1990

Journal of Microscopy

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SUMMARY The combined application of autoradiography and electron microscopy allowed the assignment of molecular components to individual micellar fibres in a mixed gel. Resolution was of the order of 0.1 μm. As a result, it was shown that bimolecular sheets of N‐dodecyl‐l‐mannonamide (= l‐Man‐12) completely separated from helical rods consisting of tritiated N‐octyl‐d‐gluconamide (= d‐Glu‐8). The method should be useful for the analysis of several other synthetic supramolecular systems.

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Lipid bilayer fibers from diastereomeric and enantiomeric N-octylaldonamides

Cited by 220 publications

References 3 publications

Structure of cholesterol helical ribbons and self-assembling biological springs

Structure of cholesterol helical ribbons and self-assembling biological springs

Low Molecular Weight Gelators for Organic Solvents

Assignment of two ultrastructures formed by a mixture of hexonamides using autoradiography and electron microscopy

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