Document Detail

Total synthesis of a cholinergic neuron-specific ganglioside GT1a alpha: a high affinity ligand for myelin-associated glycoprotein (MAG).
MedLine Citation:
PMID:  10972137     Owner:  NLM     Status:  MEDLINE    
An efficient total synthesis of a cholinergic neuron-specific ganglioside GT1a alpha (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4Cer) is described. The suitably protected sialyl-alpha(2-->6)-gangliotriose (III6NeuAc-GgOse3) derivative was glycosylated with the phenyl 2-thioglycoside of sialic acid in the presence of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethane-sulfonate (TMSOTf) in acetonitrile medium, giving the disialogangliotriose (III6NeuAcII3NeuAc-GgOse3) derivative which contains both sialyl-alpha(2-->6)-GalNAc and sialyl-alpha(2-->3)-Gal structures (Route I). This pentasaccharide was efficiently synthesized also by the coupling of (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosylonate)-(2-->6)-2-deoxy-3,4-O-isopropylidene-2-ph thalimido-D-galactopyranosyl trichloroacetimidate with 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosylonate)-(2-->3)-(2,6-di-O-benzyl-beta-D-galactopy ranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside, followed by conversion of the phthalimido group to the acetamido group (Route II). O-Deisopropylidenation and further glycosylation with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-gala ct-2-nonulopyranosylonate)-(2-->3)-2,4,6-tri-O-benzoyl-1-thio-b eta-D-galactopyranoside, promoted by dimethyl(methylthio)sulfonium triflate (DMTST), gave the desired trisialogangliotetraose (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4) derivative, which was converted stepwise into the title ganglioside GT1a alpha by the introduction of the ceramide part and then complete deprotection. The ganglioside obtained was shown to be identical with the native GT1a alpha on TLC-immunostaining.
H Ito; H Ishida; H Waki; S Ando; M Kiso
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Glycoconjugate journal     Volume:  16     ISSN:  0282-0080     ISO Abbreviation:  Glycoconj. J.     Publication Date:  1999 Oct 
Date Detail:
Created Date:  2000-09-25     Completed Date:  2000-09-25     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8603310     Medline TA:  Glycoconj J     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  585-98     Citation Subset:  IM    
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
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MeSH Terms
Carbohydrate Conformation
Carbohydrate Sequence
Cell Membrane / chemistry
Ceramides / metabolism
Cholinergic Fibers / chemistry*
Chromatography, Thin Layer
Gangliosides / chemical synthesis*,  chemistry,  metabolism*
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Myelin-Associated Glycoprotein / metabolism*
N-Acetylneuraminic Acid / metabolism
Neurons / chemistry*
Oligosaccharides / chemical synthesis,  chemistry,  metabolism
Protein Binding
Reg. No./Substance:
0/Ceramides; 0/Gangliosides; 0/Ligands; 0/Myelin-Associated Glycoprotein; 0/Oligosaccharides; 131-48-6/N-Acetylneuraminic Acid; 141255-28-9/GT1aalpha ganglioside

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