Synthesis of the Sda determinant and two analogous tetrasaccharides

Carbohydrate Research
P B van SeeventerJ F Vliegenthart

Abstract

To contribute to the possibility of studying in greater detail the biological significance of Sda-containing glycans as occur in Tamm-Horsfall glycoprotein, the following three spacer-linked tetrasaccharides have been synthesized: the Sda determinant alpha-Neu p5Ac-(2-->3)-[beta- D-GalpNAc-(1-->4)]-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH 2 (1), the Gal-analogue alpha-Neup5Ac-(2-->3)-[beta-D-Galp-(1-->4)]-beta-D-Galp-(1-->4) -beta-D-GlcpNAc-(1-->O)(CH2)5NH2 (2), and the GlcNAc-analogue alpha-Neup5Ac-(2-->3)-[beta-D-GlcpNAc-(1-->4)]- beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH2 (3). The general trisaccharide acceptor 5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy- D-glycero-alpha-D-galactonon-2-ulopyranosylonate)-(2-->3)-(2 ,6-di-O-benzyl- beta-D-galactopyranosyl)-(1-->4)-3,6-di-O- benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside was prepared, using methyl (phenyl 5- acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto- non- 2-ulopyranosid)- onate as the sialyl donor. For the syntheses of 1, 2, and 3 the glycosyl donors 3,4,6-tri-O- acetyl-2-deoxy-2-phthalimido-alpha-D-galactopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-alpha-D- galactopyranosyl bromide, and 3,4,6-tri-O-a...Continue Reading

References

Apr 10, 1991·Molecular and Cellular Biochemistry·N SathyamoorthyA Muchmore
Jun 28, 1988·Biochemistry·B K GillardD M Marcus
Nov 15, 1986·Carbohydrate Research·M SugimotoT Ogawa
Sep 15, 1983·Biochemical and Biophysical Research Communications·A S DonaldW M Watkins
Nov 15, 1984·Carbohydrate Research·J WilliamsJ F Vliegenthart
Mar 1, 1982·Carbohydrate Research·H Paulsen, A Bünsch
Apr 15, 1994·Biochemical and Biophysical Research Communications·G TomaS Kumar
Mar 1, 1994·Proceedings of the National Academy of Sciences of the United States of America·S LadischE Olson
Jan 11, 1996·Carbohydrate Research·U Ellervik, G Magnusson

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