Synthesis of ganglioside GM1 containing a thioglycosidic bond to its labeled ceramide(s). A facile synthesis starting from natural gangliosides

Schwarzmann, Günter; Hofmann, Petra; Pütz, U.

doi:10.1016/s0008-6215(97)00202-4

Cited by 21 publications

(9 citation statements)

References 22 publications

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“…Approximately 80 mg (125 µmol) sialyllactose was treated with acetic anhydride in pyridine with a catalytic amount of 4-dimethylaminopyridine at 60°C for 2 days following a procedure described previously ( 43 ). Solvents were removed azeotropically with toluene, and the remaining residue was chromatographed on silica gel in Lobar B with acetone-toluene (1:1, by volume).…”

Section: -Lactonementioning

confidence: 99%

“…1B and was prepared from deca-O -acetyl-monosialolactose-sialoyl-II 2 -lactone essentially as described for tetradeca-O -acetyl-␣ -monosialogangliotetraosyl bromide sialoyl-II 2 -lactone ( 43 ). Briefl y, under ice cooling 65 mg deca-O -acetyl-monosialolactose-sialoyl-II 2 -lactone was dissolved in 0.8 ml 30% HBr in glacial acetic acid and 8 µl acetic anhydride.…”

Section: Nona-o -Acetyl-␣ -Monosialolactosyl Bromide Sialoyl-ii 2 -Lamentioning

confidence: 99%

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Membrane-spanning lipids for an uncompromised monitoring of membrane fusion and intermembrane lipid transfer

Schwarzmann

Breiden

Sandhoff

2015

Journal of Lipid Research

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Section: -Lactonementioning

confidence: 99%

Section: Nona-o -Acetyl-␣ -Monosialolactosyl Bromide Sialoyl-ii 2 -Lamentioning

confidence: 99%

Membrane-spanning lipids for an uncompromised monitoring of membrane fusion and intermembrane lipid transfer

Schwarzmann

Breiden

Sandhoff

2015

Journal of Lipid Research

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“…Third, stilbene is not prone to isomerizations because the phenyl group stops the migration of the double bond. In the fi rst step, 2 was peracetylated by a modifi ed method of Schwarzmann, Hofmann, and Pütz ( 43 ). These reaction conditions led to the formation of lactone 23 in a yield of 62%.…”

Section: Downloaded Frommentioning

confidence: 99%

Partial synthesis of ganglioside and lysoganglioside lipoforms as internal standards for MS quantification

Gantner

Schwarzmann

Sandhoff

et al. 2014

Journal of Lipid Research

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Nonnatural ganglioside and lysoganglioside lipoforms 2693 MATERIALS AND METHODS MaterialsAll chemicals were of analytical grade or the highest purity available. Water (H 2 O) used for buffers and solutions was purifi ed by an ultrapure H 2 O system (EASYpure UV/UF D8612, Werner Reinstwassersysteme, Leverkusen, Germany). Solvents used in reactions of oxygen-and moisture-sensitive compounds were in anhydrous form. 1-Propanol, methanol (MeOH), pyridine, and acetic anhydride were degassed before use. The native mixture of bovine brain gangliosides, Cronassial ® , which consists of 21% GM1, 40% GD1a, 16% GD1b, 19% GT1b, and 4% other gangliosides ( 25 ), was available in our lab. Sphingolipid ceramide N -deacylase (SCDase) and ␤ -galactosidase from bovine testes were from Sigma-Aldrich (Schnelldorf, Germany). Triton™ X-100, sodium taurodeoxycholate, Grubbs catalyst 2nd generation, HoveydaGrubbs catalyst 2nd generation, and Stewart-Grubbs catalyst were also from Sigma-Aldrich. For normal phase (NP) column chromatography, silica gel 60 (0.040-0.063 mm or 0.015-0.040 mm) from Merck (Darmstadt, Germany) was used. For desalting and reversed phase (RP) column chromatography, LiChroprep ® RP-18 (0.040-0.063 mm) from Merck was used. For TLC analysis, highperformance TLC (HPTLC) silica gel 60 F 254 and HPTLC silica gel 60 RP-18 plates from Merck were used. For anion-exchange chromatography, DEAE Sephadex™ A-25 from Amersham Pharmacia Biotech AB (Uppsala, Sweden) was used. Purifi cationDesalting was performed by the method of Wiliams and McCluer ( 26 ). The usage of polar eluents for column chromatography causes signifi cant contamination of column material in the products. We reduced this contamination to a minimum by the following method. NP silica gel columns of a very small column volume (approximately 1 ml column volume per 5 mg of product) were prepared in fi ltration columns from Supelco (Bellefonte, PA) using a mobile phase in which the substance is retained on the column. The substance was applied to the column and washed with three column volumes of the same solvent. Then, the substance was eluted by an appropriate solvent of higher polarity. C-NMR spectroscopy, Bruker Avance 300, 400, or 500 instruments (Billerica, MA) were used. For exchange of exchangeable protons by deuterium, gangliosides were dissolved in CD 3 OD and the solvent was removed in a stream of nitrogen. This process was repeated three times before measurement. For EI-MS, a MAT 95 XL sector fi eld instrument (Thermo Finnigan MAT GmbH, Bremen, Germany) or a MAT 90 sector fi eld instrument gangliosidosis ( 22 ). Both substances are potential biomarkers for these diseases ( 23 ), and the lysoganglioside standards prepared in this work can be used for their quantitative analysis. Analytical proceduresQuantifi cation of gangliosides by MS, including quantitative imaging MS, requires calibration substances. Hereby, calibration is defined as the establishment of a correlation between analyte concentration and mass spectrometer response. Three principle meth...

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“…Substitution of the oxygen in a glycosidic linkage with a sulfur atom is known to lead to resistance to glycosidases (36)(37)(38). Thus we targeted the synthesis of TMR-labeled thiolactosylsphingolipid 1 to focus on anabolic pathways (Scheme 1) (39).…”

Section: Development Of Catabolically Stable Gsl Analogsmentioning

confidence: 99%

Application of Fluorescently-Labeled Glycosphingolipids to Metabolic Profiling in Single Cells Using Capillary Electrophoresis

Yoshimura

Tanaka

Dovic̀hi

et al. 2012

TIGG

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Glycosphingolipids (GSLs) are important components expressed at the cell surface, where they play numerous roles in biological processes. The analysis of GSL metabolism is important but remains challenging in part due to the complexity of the components. To better understand the functions of GSLs on single cell scale we are developing an analytical method that uses fluorescently-tagged GSL analogs and capillary electrophoresis with laser induced fluorescence detection. We are applying this method to monitor glycolipid metabolism in single cells. In this article, we summarize our methodology, show examples of the chemoenzymatic synthesis of glycolipid analogs, and provide some experimental data in single cell analysis.

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Synthesis of ganglioside GM1 containing a thioglycosidic bond to its labeled ceramide(s). A facile synthesis starting from natural gangliosides

Cited by 21 publications

References 22 publications

Membrane-spanning lipids for an uncompromised monitoring of membrane fusion and intermembrane lipid transfer

Membrane-spanning lipids for an uncompromised monitoring of membrane fusion and intermembrane lipid transfer

Partial synthesis of ganglioside and lysoganglioside lipoforms as internal standards for MS quantification

Application of Fluorescently-Labeled Glycosphingolipids to Metabolic Profiling in Single Cells Using Capillary Electrophoresis

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