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[Synthesis of a highly branched nonasaccharide sequence of the "bisected"structure of N-glycoproteins].

作者信息

Paulsen H, Heume M, Nürnberger H

机构信息

Institut für Organische Chemie, Universität Hamburg, Bundesrepublik Deutschland.

出版信息

Carbohydr Res. 1990 Apr 25;200:127-66. doi: 10.1016/0008-6215(90)84187-y.

DOI:10.1016/0008-6215(90)84187-y
PMID:2379203
Abstract

A highly branched nonasaccharide, beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----2)-alpha-D-Manp-(1----3) -[beta-D- Glcp-NAc-(1----4)-[beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----2)-alpha-D- Manp- (1----6)]-beta-D-Manp-(1----4)-D-GlcNAc, that represents the carbohydrate chain of the "bisected" structure of lactosamine-type N-glycoproteins was synthesized by a block synthesis approach. The activated trisaccharide block beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----2)-D-Man was coupled first with the low reactive OH-3 group and, in a second step, with the reactive OH-6 group of the central beta-D-mannopyranosyl residue within the suitably protected trisaccharide block beta-D-GlcpNAc-(1----4)-beta-D-Manp-(1----4)-D-GlcNAc. During these coupling steps, the alpha-glycosidic linkages of D-mannopyranosyl residues were formed without neighboring-group participation, which is only successful by use of the imidate procedure.

摘要

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Carbohydr Res. 1990 Apr 25;200:127-66. doi: 10.1016/0008-6215(90)84187-y.
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