skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: New trends in ganglioside chemistry

Abstract

New methods have been developed for the preparation of highly purified gangliosides, homogeneous in the saccharide, long chain base, and fatty acid moieties and gangliosides carrying different kinds of labelled probes. Gangliosides, homogeneous in the oligosaccharide portion, were prepared by preparative normal phase HPLC on a Lichrosorb-NH-2 column, using a gradient of acetonitrile-phosphate buffer, pH 5.6, as solvent system. Each class of ganglioside (from monosialo- to tetrasialogangliosides) was then submitted to reversed phase HPLC on a preparative RP-8 column, using acetonitrile-5 mM phosphate buffer, pH 7, as solvent system, to obtain gangliosides homogeneous in the long chain base moiety. Gangliosides containing C18 and C20 sphinganine were prepared by catalytic hydrogenation of the corresponding unsaturated gangliosides. GM1 with homogeneous acyl chain was prepared by alkaline hydrolysis in the presence of tetramethylammonium hydroxide, followed by re-N-acylation, carried out in the presence of dimethylaminopropyl, ethylcarbodiimide and natural fatty acids, or of mixed anhydride of ethylchloroformate and 14C-stearic acid, and re-N-acetylation performed with acetic anhydride or labelled acetic anhydride. The GM1 derivative, de-acetylated at the level of sialic acid, also produced by alkaline treatment of GM1, was submitted to re-N-acetylation with 14C-acetic anhydride to produce specifically 14C-labelled GM1. Re-N-acylation was carried out a) inmore » the presence of dimethylaminopropyl, ethylcarbodiimide and natural fatty acids, b) with mixed anhydride of ethylchloroformate and 14C-stearic acid. After re-N-acylations, re-N-acetylation was performed with acetic anhydride or labelled acetic anhydride. 53 references.« less

Authors:
; ; ; ;
Publication Date:
Research Org.:
Univ. of Milan (Italy)
OSTI Identifier:
6583311
Resource Type:
Journal Article
Journal Name:
Adv. Exp. Med. Biol.; (United States)
Additional Journal Information:
Journal Volume: 228
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; GANGLIOSIDES; CHEMICAL PREPARATION; CARBON 14 COMPOUNDS; LIQUID COLUMN CHROMATOGRAPHY; NERVOUS SYSTEM; OLIGOSACCHARIDES; TRACER TECHNIQUES; CARBOHYDRATES; CHROMATOGRAPHY; GLYCOLIPIDS; ISOTOPE APPLICATIONS; LABELLED COMPOUNDS; LIPIDS; ORGANIC COMPOUNDS; SACCHARIDES; SEPARATION PROCESSES; SYNTHESIS; 550201* - Biochemistry- Tracer Techniques

Citation Formats

Sonnino, S, Ghidoni, R, Gazzotti, G, Acquotti, D, and Tettamanti, G. New trends in ganglioside chemistry. United States: N. p., 1988. Web. doi:10.1007/978-1-4613-1663-3_16.
Sonnino, S, Ghidoni, R, Gazzotti, G, Acquotti, D, & Tettamanti, G. New trends in ganglioside chemistry. United States. https://doi.org/10.1007/978-1-4613-1663-3_16
Sonnino, S, Ghidoni, R, Gazzotti, G, Acquotti, D, and Tettamanti, G. 1988. "New trends in ganglioside chemistry". United States. https://doi.org/10.1007/978-1-4613-1663-3_16.
@article{osti_6583311,
title = {New trends in ganglioside chemistry},
author = {Sonnino, S and Ghidoni, R and Gazzotti, G and Acquotti, D and Tettamanti, G},
abstractNote = {New methods have been developed for the preparation of highly purified gangliosides, homogeneous in the saccharide, long chain base, and fatty acid moieties and gangliosides carrying different kinds of labelled probes. Gangliosides, homogeneous in the oligosaccharide portion, were prepared by preparative normal phase HPLC on a Lichrosorb-NH-2 column, using a gradient of acetonitrile-phosphate buffer, pH 5.6, as solvent system. Each class of ganglioside (from monosialo- to tetrasialogangliosides) was then submitted to reversed phase HPLC on a preparative RP-8 column, using acetonitrile-5 mM phosphate buffer, pH 7, as solvent system, to obtain gangliosides homogeneous in the long chain base moiety. Gangliosides containing C18 and C20 sphinganine were prepared by catalytic hydrogenation of the corresponding unsaturated gangliosides. GM1 with homogeneous acyl chain was prepared by alkaline hydrolysis in the presence of tetramethylammonium hydroxide, followed by re-N-acylation, carried out in the presence of dimethylaminopropyl, ethylcarbodiimide and natural fatty acids, or of mixed anhydride of ethylchloroformate and 14C-stearic acid, and re-N-acetylation performed with acetic anhydride or labelled acetic anhydride. The GM1 derivative, de-acetylated at the level of sialic acid, also produced by alkaline treatment of GM1, was submitted to re-N-acetylation with 14C-acetic anhydride to produce specifically 14C-labelled GM1. Re-N-acylation was carried out a) in the presence of dimethylaminopropyl, ethylcarbodiimide and natural fatty acids, b) with mixed anhydride of ethylchloroformate and 14C-stearic acid. After re-N-acylations, re-N-acetylation was performed with acetic anhydride or labelled acetic anhydride. 53 references.},
doi = {10.1007/978-1-4613-1663-3_16},
url = {https://www.osti.gov/biblio/6583311}, journal = {Adv. Exp. Med. Biol.; (United States)},
number = ,
volume = 228,
place = {United States},
year = {Fri Jan 01 00:00:00 EST 1988},
month = {Fri Jan 01 00:00:00 EST 1988}
}