| Ganglioside GD1 alpha analogues as high-affinity ligands for myelin-associated glycoprotein (MAG). | |
| | |
MedLine Citation:
|
PMID: 10420586 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
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. |
| | |
Authors:
|
N Sawada; H Ishida; B E Collins; R L Schnaar; M Kiso |
Related Documents
:
|
6768796 - Biosynthesis of lymphocyte surface igd in the mouse. 2456756 - Purification and characterization of a differentiation-specific sialoglycoprotein of la... 20460706 - Synthesis of gamma-lactone-type sialic acid, an isomer of 2,3-dehydrosialic acid. 2010546 - Sialic acid storage diseases. a multiple lysosomal transport defect for acidic monosacc... 11374996 - Study of the addition of monoalkylphosphonic acids onto trialkyl-substituted epoxides. 16376896 - High-performance liquid chromatography method for simultaneous determination of aliphat... |
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 |
Affiliation:
|
Department of Applied Bio-organic Chemistry, Gifu University, Japan. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Animals COS Cells Carbohydrate Sequence Cercopithecus aethiops G(M1) Ganglioside / analogs & derivatives*, metabolism Glycosylation Ligands Molecular Sequence Data Myelin-Associated Glycoprotein / metabolism* Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
|
0/Ligands; 0/Myelin-Associated Glycoprotein; 101839-44-5/ganglioside GD1alpha; 37758-47-7/G(M1) Ganglioside |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Sequence analysis of the Gluconobacter oxydans RecA protein and construction of a recA-deficient mut...
Next Document: Synthesis and antitumor activity of 7-O-[2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-alpha-L-talopyra...