Molecular and crystal structure of the bola-amphiphile N-[8-(d-gluconamido)octyl]-d-gluconamide

Müller‐Fahrnow, Anke; Fritsch, Detlev; Schnieder, Peter; Fuhrhop, Jürgen‐Hinrich

doi:10.1016/0008-6215(93)80018-a

Cited by 29 publications

(7 citation statements)

References 10 publications

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“…Surfactants of the type di(C 6 -Glu) may be synthesized from renewable resources and, for this reason, have aroused much recent interest. [5][6][7][8][9] Eastoe et al have measured the surface tension, micellar structure, and binary surfactant-water phase diagram of di(C 6 -Glu) and have shown that the material exhibits classical nonionic behavior in dilute aqueous solution. 10 Surface tension measurements cannot, however, provide information on the structural properties of surfactant systems at interfaces.…”

Section: Introductionmentioning

confidence: 99%

Neutron Reflection Study of a Double-Chained Sugar Surfactant

Cooke¹,

Lu²,

Lee³

et al. 1996

J. Phys. Chem.

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Neutron reflection and surface tension have been used to investigate the structural features exhibited at the air-liquid interface by an adsorbed layer of the sugar-based nonionic surfactant 7,7-bis [(1,2,3,4,5pentahydroxyhexanamido)methyl]-n-tridecane. It consists of two glucamide headgroups and two C 6 H 13 alkyl chains, i.e., (C 6 H 13 ) 2 C(CH 2 NHCO(CHOH) 4 CH 2 OH) 2 , abbreviated to di(C 6 -Glu). Isotopic substitution was used to distinguish the chains of the surfactant from the headgroup and solvent distributions. The critical micelle concentration (CMC) was found to be (1.9 ( 0.1) × 10 -3 M using surface tension measurements, and the latter also indicated that the surface properties were not affected by isotopic substitution. The specular reflection of neutrons has been used to determine the surface concentrations of skeletally deuterated di(C 6 -Glu) over the concentration range CMC/400 to 2CMC. The neutron measurements showed the area per molecule A at the CMC to be 66 ( 3 Å 2 , as compared with 60 ( 10 Å 2 from surface tension measurements. The layer structure has been determined using three different isotopic contrasts at concentrations of CMC and CMC/400. The fit of a two-layer model shows that the total monolayer thickness decreases from 17.5 ( 1.5 Å at the CMC to 14.5 ( 1.5 Å at CMC/400, respectively. The kinematic approximation was used to fit the neutron data and an X-ray reflection profile. The most remarkable feature of the structure obtained is the apparent smoothness of the layer. The calculated roughness of the layer at the CMC is 9.7 Å 2 which corresponds exactly to the value expected for capillary waves using the model of a pure liquid. At the CMC the molecule as a whole appears to be tilted about 35-40°away from the surface normal, but at CMC/400 the hydrocarbon chains are approximately normal to the surface while the gluconamide groups are strongly tilted.

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Section: Introductionmentioning

confidence: 99%

Neutron Reflection Study of a Double-Chained Sugar Surfactant

Cooke¹,

Lu²,

Lee³

et al. 1996

J. Phys. Chem.

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“…1). The polar groups include glycerol and related polyols and are connected to the hydrophobic chain through ether, acetal, ester, and amide links (347). Compounds of type A can form micelles or monolayer lipid vesicles for a range of variants in the structure, but more complex behavior has been observed for bis(azacrown ether) bola-amphiphiles (micelle or multilamellar vesicle formation depending on the length of the spacer group) (348).…”

Section: Unusual Bolaform Amphiphilesmentioning

confidence: 98%

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Dembitsky

2005

Lipids

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Polyether glycosidic ionophores and macrocyclic glycosides are of great interest, especially for the medicinal and pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antibiotics, anticancer agents, or in industry. More than 300 interesting and unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

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“…It can be seen that these three bola surfactants significantly reduced the surface tension at low concentration, indicating that these molecules adsorbed strongly at the air-water interface. c CMC values are 23-25 mN m -1 , significantly lower than those conventional hydrocarbon-based bola surfactants [1,2]. This result may be attributed to the siloxane methyl groups in the hydrophobic part lying flat at the air-water interface [32][33][34].…”

Section: Equilibrium Surface Tension and Critical Micelle Concentrationmentioning

confidence: 99%

“…Bola surfactants consisting of two or more hydrophilic groups connected by a hydrophobic spacer have attracted great attention because of their fundamental importance and their potential applicability [1,2]. Most of these bola surfactants have been studied for their aggregate behavior in water as a function of their structure [3,4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Solution Properties of Carbohydrate‐Modified Polysiloxane Bola Surfactants

Zeng

Wang

Chen

et al. 2015

J Surfact & Detergents

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Three carbohydrate-modified polysiloxane bola surfactants (ATPS-GA) were synthesized using a two-step method. Their chemical structures were characterized by infrared spectroscopy (FT-IR) and proton nuclear magnetic resonance spectroscopy ( 1 H NMR). Their surface properties and aggregation properties in aqueous solution were determined using surface tension measurements and transmission electron microscopy (TEM). Surface tension measurement results indicated that the three bola surfactants are under 25 mN m -1 , and much lower than those of conventional hydrocarbon bola surfactants due to the siloxane moiety at the end of the hydrophobic chains. TEM analysis results indicated that the ATPS-GA can selfassemble into spherical micelles with a wide range of average diameters from 100 nm to above 600 nm.

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Molecular and crystal structure of the bola-amphiphile N-[8-(d-gluconamido)octyl]-d-gluconamide

Cited by 29 publications

References 10 publications

Neutron Reflection Study of a Double-Chained Sugar Surfactant

Neutron Reflection Study of a Double-Chained Sugar Surfactant

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Synthesis and Solution Properties of Carbohydrate‐Modified Polysiloxane Bola Surfactants

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