SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES-53 - SYNTHESIS OF NOVEL N-METHYL-1-DEOXYNOJIRIMYCIN-CONTAINING SIALO-OLIGOSACCHARIDES RELATED TO GANGLIOSIDE GM3 ACTIVE AS A BIOSIGNAL MEDIATOR

Authors
KISO M KATAGIRI H FURUI H ANDO K ISHIDA H HASEGAWA A
Citation
M. Kiso et al., SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES-53 - SYNTHESIS OF NOVEL N-METHYL-1-DEOXYNOJIRIMYCIN-CONTAINING SIALO-OLIGOSACCHARIDES RELATED TO GANGLIOSIDE GM3 ACTIVE AS A BIOSIGNAL MEDIATOR, Journal of carbohydrate chemistry, 13(2), 1994, pp. 163-174
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
13
Issue
2
Year of publication
1994
Pages
163 - 174
Database
ISI
SICI code
0732-8303(1994)13:2<163:SSOS-S>2.0.ZU;2-U
Abstract
O-(6-O-Benzoyl-beta-D-galactopyranosyl)-(1-->4)- and O-(2,3,4-tri-O-ac etyl-beta-D-galactopyranosyl)- enzyloxycarbonyl-1,5-dideoxy-1,5-imino- D-glucitols (4 and 12) were each coupled with methyl (methyl 5-acetami do-4,7,8, 9-tetra-O-acetyl-3, 2-thio-D-glycero-D-galacto-2-nonulopyran osid)onate (5) in acetonitrile medium in the presence of dimethyl(meth ylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethan esulfonic acid to give the corresponding alpha-sialyl-(2-->3)- and alp ha-sialyl-(2-->6)-glycosides (6 and 13 alpha), which were converted to novel ganglioside GM3-related trisaccharides (9 and 15) containing N- methyl-1-deoxynojirimycin.