ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Building Units of Oligosaccharides, XLVII. - Synthesis of Tri- and Tetrasaccharide Sequences of N-Glycoproteins Including a β-D-Mannosidic LinkageThe trisaccharides α-D-Man-p-(1 → 6)-β-D-Man-p-(1 → 4)-D-GlcNAc (37) and α-D-Man-p-(1 → 3)-β-D-Man-p-(1 → 4)-D-GlcNAc (43) as well as the key tetrasaccharide α-D-Man-p-(1 → 3)-[α-Man-p-(1 → 6)]-β-D-Man-p-(1 → 4)-D-GlcNAc (51), which are parts of the carbohydrate chain of N-glycoproteins, have been synthesized. In this case the most important reaction is the direct synthesis of a β-mannoside linkage of D-mannos with 2-acetamido-2-deoxy-D-glucose. This problem has been solved by coupling of the halide 10 with the hydroxy component 14 in the presence of silver silicate which leads to the disaccharide 17. The product 17 is the fundamental compound for building up more complexed oligosaccharides.
Notes:
Die im Kohlenhydrat-Teil von N-Glycoproteinen enthaltenen Trisaccharide α-D-Man-p-(1 → 6)-β-D-Man-p-(1 → 4)-D-GlcNAc (37) und α-D-Man-p-(1 → 3)-β-D-Man-p-(1 → 4)-D-GlcNAc (43) und das Schlüsseltetrasaccharid α-D-Man-p-(1 → 3)-[α-D-Man-p-(1 → 6)]-β-D-Man-p-(1 → 4)-D-GlcNAc (51) wurden synthetisiert. Die wichtigste Reaktion ist hierbei die direkte Herstellung der β-D-mannosidischen Verknüpfung zwischen D-Mannose und 2-Acetamido-2-desoxy-D-glucose. Die Verknüpfung gelingt durch Umsetzung des Halogenids 10 und der Hydroxylkomponente 14 mit Hilfe des Silbersilicat-Verfahrens zum Disaccharid 17. Das Produkt 17 ist die Schlüsselsubstanz für alle weiteren Aufbaureaktionen zu höheren Oligosacchariden.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198319830617
