Document Detail

Ganglioside GD1 alpha analogues as high-affinity ligands for myelin-associated glycoprotein (MAG).
MedLine Citation:
PMID:  10420586     Owner:  NLM     Status:  MEDLINE    
The first systematic synthesis of ganglioside GD1 alpha analogues carrying N-acetyldeoxyneuraminic acids linked to C-6 of the GalNAc residue was accomplished. The suitably protected GM1b pentasaccharide derivative was regioselectively glycosylated with the phenyl 2-thioglycosides of 7-deoxy, 8-deoxy, and 9-deoxy-N-acetylneuraminic acid promoted by N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) in acetonitrile, and the resulting hexasaccharides were converted to the target GD1 alpha analogues. All of the analogues retained excellent efficiency in supporting the adhesion to myelin-associated glycoprotein (MAG), raising the possibility that the internal sialic acid linked to the GalNAc residue may be replaced by other anionic substituents, in contrast to the terminal sialic acid, which is essential for MAG binding.
N Sawada; H Ishida; B E Collins; R L Schnaar; M Kiso
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  316     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1999 Mar 
Date Detail:
Created Date:  1999-10-05     Completed Date:  1999-10-05     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  1-5     Citation Subset:  IM    
Department of Applied Bio-organic Chemistry, Gifu University, Japan.
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MeSH Terms
COS Cells
Carbohydrate Sequence
Cercopithecus aethiops
G(M1) Ganglioside / analogs & derivatives*,  metabolism
Molecular Sequence Data
Myelin-Associated Glycoprotein / metabolism*
Structure-Activity Relationship
Reg. No./Substance:
0/Ligands; 0/Myelin-Associated Glycoprotein; 101839-44-5/ganglioside GD1alpha; 37758-47-7/G(M1) Ganglioside

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