Document Detail

Preparation of GM1 ganglioside molecular species having homogeneous fatty acid and long chain base moieties.
MedLine Citation:
PMID:  3989384     Owner:  NLM     Status:  MEDLINE    
A new procedure is described for preparing the molecular species of GM1 ganglioside that carry a single fatty acid (myristic (C14:0), stearic (C18:0), arachidic (C20:0) or lignoceric (C24:0) acid) and a single long chain base (C18 or C20 sphingosine, C18 or C20 sphinganine, each of them in natural 3D(+)erythro or unnatural 3L(-)threo form). The procedure consisted of the following steps: a) alkaline hydrolysis of GM1 ganglioside in the presence of tetramethylammonium hydroxide, which produces de-N-acylation of the ceramide and de-N-acetylation of the sialic acid residue; b) specific re-N-acylation at the long chain base amino group with a new fatty acid (myristic, stearic, arachidic, or lignoceric) in the presence of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride; and c) final re-N-acetylation at the level of the sialic acid residue. GM1 ganglioside molecular species, completely homogeneous in the ceramide portion, were prepared by reversed phase high performance liquid chromatography. The GM1 ganglioside molecular species were analyzed for saccharide, fatty acid, and long chain base composition by chemical and spectrometric analyses. Using a combination of the two procedures, 32 different molecular species of GM1 ganglioside, over 99% homogeneous, have been prepared.
S Sonnino; G Kirschner; R Ghidoni; D Acquotti; G Tettamanti
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of lipid research     Volume:  26     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  1985 Feb 
Date Detail:
Created Date:  1985-06-06     Completed Date:  1985-06-06     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  248-57     Citation Subset:  IM    
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MeSH Terms
Chemical Phenomena
Chromatography, High Pressure Liquid
Fatty Acids
G(M1) Ganglioside / chemical synthesis*,  isolation & purification
Gangliosides / chemical synthesis*
Reg. No./Substance:
0/Fatty Acids; 0/Gangliosides; 37758-47-7/G(M1) Ganglioside

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