An efficient and stereoselective synthesis of 1,2-0-dialkyl-3-0-β-d-dlycosyl-sn-glycerols

Six, Lambert; Rueβ, Klaus-Peter; Liefländer, Manfred

doi:10.1016/s0040-4039(00)81621-4

Cited by 40 publications

(16 citation statements)

References 7 publications

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“…This is in part due to the difficulty of obtaining a sufficient amount of chemically pure compounds either from natural membrane extracts or by synthetic methods. Though the synthetic approach has proved promising in preparing well-defined compounds, − the procedures to obtain stereochemically pure compounds are still demanding so that the kinds of oligosaccharide head groups so far synthesized and examined have been mainly mono- and disaccharides.…”

Section: Introductionmentioning

confidence: 99%

The Effects of Oligosaccharide Stereochemistry on the Physical Properties of Aqueous Synthetic Glycolipids

Hato

Minamikawa

1996

Langmuir

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Effects of the stereochemistry of oligosaccharide head groups on the physical properties of aqueous synthetic glycolipids, 1,3-di-O-dodecyl-2-(β-glycosyl)glycerols bearing cellooligosaccharides (β-1,4-Oglycosidic bonds) and maltooligosaccharides (R-1,4-O-glycosidic bonds) as hydrophilic groups have been studied. The increase in the number of glucose residues, N, in the two different headgroups exhibited opposite effects on the physical properties of the aqueous glycolipids. For the maltooligosaccharide-containing lipid, Mal N(C12)2, increasing N in the head groups decreases the hydrated solid/liquid crystalline phase transition temperature Tm and increases the "hydrophilicity" of the lipids. However, the Tm of the cellooligosaccharide-containing lipids CelN(C12)2 increases with increasing N of the cellooligosaccharide head groups. It is noteworthy that Tm jumps from 59 °C (for N ) 4) to above 160 °C (N ) 5), so that the Cel5(C12)2 cannot form a liquid crystalline phase and was totally insoluble in water. The results can be explained in terms of different conformations of the head groups, i.e., a "helical" conformation of the maltooligosaccharides and an "extended" conformation of the cellooligosaccharides.

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Section: Introductionmentioning

confidence: 99%

The Effects of Oligosaccharide Stereochemistry on the Physical Properties of Aqueous Synthetic Glycolipids

Hato

Minamikawa

1996

Langmuir

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“…A synthetic route of glycolipids has been developed to prepare chemically well-defined glycolipids, − and the physicochemical properties of these synthetic glycolipids have been reported. − Recently, our research group developed an efficient route to synthesize glycolipids in a good yield and good stereoselectivity …”

Section: Introductionmentioning

confidence: 99%

Phase Transition in Glycolipid Monolayers Induced by Attractions between Oligosaccharide Head Groups

et al. 1996

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The surface property of two kinds of synthetic glyceroglycolipids was investigated to confirm the stereoeffect of sugar residues on the phase behavior in monolayers: one is the maltooligosaccharide-containing lipids [Mal N (C12)2] and the other is cellooligosaccharide-containing lipids [Cel N (C12)2]. The two kinds of glycolipids exhibit the opposite dependence of the surface pressure−area (Π−A) isotherm on the number of glucose residues (N), in that Mal N (C12)2 tends to be more expanded as N increases, while Cel N (C12)2 tends to be more condensed. The liquid-expanded/liquid-condensed phase transition in Cel4(C12)2 was evaluated by the Brewster angle microscopy and the latent heat analysis with the Clausius−Clapeyron equation, as a model of film condensation induced by the attraction between oligosaccharide head groups. The film morphology of Cel4(C12)2 was unique in that it exhibits the optically isotropic and flexible fluid type of the LC phase, while Glc(C16)2 forms a two-dimensional tilted crystalline phase in the same way as fatty acids and phospholipids. The heat of transition (ΔH) of Cel4(C12)2 does not converge toward zero even at high temperature. In other words, the main transition of Cel4(C12)2 does not become second order in contrast to the behavior usually encountered in monolayers. The refractive index of the oligosaccharide head groups in water as well as the alkyl chains in air must be properly taken into account to interpret the reflectivity.

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“…Monomolecular films at the water/air interface were conducted with and compared from three ether lipids, MPL, DPhG, DPhGG [49]. Collapse pressure of MPL was 39 mN/m 2 , DPhG 25 mN/m 2 , DPhGG 48 mN/m 2 , values correspond to those published for ester [50] and ether lipids [51], in case that collapse occurred directly from the liquid-expanded state of the lipids. From liquid-condensed state, collapse pressures for these lipids were around 70 mN/m 2 .…”

Section: Model Membranesmentioning

confidence: 66%

The Main (Glyco) Phospholipid (MPL) of Thermoplasma acidophilum

Freisleben

2019

IJMS

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The main phospholipid (MPL) of Thermoplasma acidophilum DSM 1728 was isolated, purified and physico-chemically characterized by differential scanning calorimetry (DSC)/differential thermal analysis (DTA) for its thermotropic behavior, alone and in mixtures with other lipids, cholesterol, hydrophobic peptides and pore-forming ionophores. Model membranes from MPL were investigated; black lipid membrane, Langmuir-Blodgett monolayer, and liposomes. Laboratory results were compared to computer simulation. MPL forms stable and resistant liposomes with highly proton-impermeable membrane and mixes at certain degree with common bilayer-forming lipids. Monomeric bacteriorhodopsin and ATP synthase from Micrococcus luteus were co-reconstituted and light-driven ATP synthesis measured. This review reports about almost four decades of research on Thermoplasma membrane and its MPL as well as transfer of this research to Thermoplasma species recently isolated from Indonesian volcanoes.

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An efficient and stereoselective synthesis of 1,2-0-dialkyl-3-0-β-d-dlycosyl-sn-glycerols

Cited by 40 publications

References 7 publications

The Effects of Oligosaccharide Stereochemistry on the Physical Properties of Aqueous Synthetic Glycolipids

The Effects of Oligosaccharide Stereochemistry on the Physical Properties of Aqueous Synthetic Glycolipids

Phase Transition in Glycolipid Monolayers Induced by Attractions between Oligosaccharide Head Groups

The Main (Glyco) Phospholipid (MPL) of Thermoplasma acidophilum

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