| Total synthesis of a cholinergic neuron-specific ganglioside GT1a alpha: a high affinity ligand for myelin-associated glycoprotein (MAG). | |
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MedLine Citation:
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PMID: 10972137 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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H Ito; H Ishida; H Waki; S Ando; M Kiso |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Glycoconjugate journal Volume: 16 ISSN: 0282-0080 ISO Abbreviation: Glycoconj. J. Publication Date: 1999 Oct |
Date Detail:
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Created Date: 2000-09-25 Completed Date: 2000-09-25 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8603310 Medline TA: Glycoconj J Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 585-98 Citation Subset: IM |
Affiliation:
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Department of Applied Bioorganic Chemistry, Gifu University, Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Carbohydrate Conformation Carbohydrate Sequence Cell Membrane / chemistry Ceramides / metabolism Cholinergic Fibers / chemistry* Chromatography, Thin Layer Gangliosides / chemical synthesis*, chemistry, metabolism* Glycosylation Ligands Magnetic Resonance Spectroscopy Molecular Sequence Data Myelin-Associated Glycoprotein / metabolism* N-Acetylneuraminic Acid / metabolism Neurons / chemistry* Oligosaccharides / chemical synthesis, chemistry, metabolism Protein Binding |
| Chemical | |
Reg. No./Substance:
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0/Ceramides; 0/Gangliosides; 0/Ligands; 0/Myelin-Associated Glycoprotein; 0/Oligosaccharides; 131-48-6/N-Acetylneuraminic Acid; 141255-28-9/GT1aalpha ganglioside |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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