- New GM1 ganglioside derivatives for selective single and double labelling of the natural glycosphingolipid skeleton
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Selective single and double labelling of the natural ganglioside GM1. enables one to introduce various markers into different parts of the glycosphingolipid molecule without changing the natural skeleton. To that end, N-Fmoc-2amino-, N-Fmoc-18-amino- and S-(ethoxythiocarbonyl)-18mercaptostearic acids have been prepared, and. coupled with the primary amino group in the sphingosine part of lyso-GM1 and. deAc-deAcyl-GM1. gangliosides. The products of these coupling reactions - building blocks 16a, 16b, 16c, 26 and 27 - may be used for the synthesis of GM1 derivatives with one or two fluorescent dye moieties or other labels of various polarities. Examples of various labelling strategies, using hydrophilic and lipophilic photostable fluorescent dyes, have been made available. The GM1. derivatives 17a, 22a and 23c labelled with the fluorescent dye ATTO 647N or the doubly labelled derivative 25b can be used as probes in fluorescence correlation spectroscopy (in conventional, microscopy or stimulated emission depletion nanoscopy) to study the diffusion of lipid analogues in model or live cell membranes.
- Polyakova, Svetlana M.,Belov, Vladimir N.,Yan, Sergey F.,Eggeling, Christian,Ringemann, Christian,Schwarzmann, Guenter,De Meijere, Armin,Hell, Stefan W.
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supporting information; experimental part
p. 5162 - 5177
(2010/01/11)
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- Process of preparing ω-hydroxy acids
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A new synthesis of ω-hydroxy acids, which employs commercially available starting materials and lowers the cost of production. The process involves coupling a fatty acyl group by enamine chemistry, followed by a ring expansion and selective reduction of ketoacid.
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- Acides gras marques en position ω par un nucleide radioactif emetteur γ
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The synthesis of many saturated, acetylenic, olefinic (Z or E) fatty acids labeled with 123I or 131I at the ω-position has been achieved.The radioactive iodine atom is introduced by a I-, *I- exchange reaction; the influence on the yield of several parameters - presence of iodine carrier, fatty acid and water concentrations, solution acidity - has been studied.Experimental conditions which produce labeling yields higher than 95percent have been defined; these results have lead to a very easy labeling method used in several hospitals in the external study of myocardial metabolism of fatty acids.
- Riche, Francoise,Mathieu, Jean-Paul,Vincens, Maurice,Bardy, Andre,Comet, Michel,Vidal, Michel
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