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Bausteine von Oligosacchariden, CIV. Synthese von verzweigten Tetrasaccharid‐ und Pentasaccharid‐Strukturen von N ‐Glycoproteinen, methyliert an 4′‐OH des Verzweigungsgliedes
Author(s) -
Paulsen Hans,
Wilkens Roland,
Reck Folkert,
Brockhausen Inka
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201215
Subject(s) - tetrasaccharide , chemistry , stereochemistry , glycosidic bond , trisaccharide , polysaccharide , biochemistry , enzyme
Building Units of Oligosaccharides, CIV. — Synthesis of Branched Tetrasaccharide and Pentasaccharide Structures of N ‐Glycoproteins Methylated at 4′‐OH of the Branching Unit The tetrasaccharide α‐ D ‐Man p ‐(1→3)[α‐ D ‐Man p ‐(1→6)]‐4‐ O ‐methyl‐β‐ D ‐Man p ‐(1→4)‐ D ‐GlcNAc ( 15 ) and the pentasaccharide β‐ D ‐Glc p NAc‐(1→2)‐α‐ D ‐Man p ‐ (→3)[α‐ D ‐Man p ‐(→6)]‐4‐ O ‐methyl‐β‐ D ‐Man p ‐ (→4)‐ D ‐GlcNAc ( 23 ) were synthesized by adding the respective functionalized building blocks. The compounds are useful for studies of the substrate specificities of GlcNAc transferases I and II in the biosynthesis of N‐linked oligosaccharides, respectively. In addition we developed an effective synthesis for the β‐glycosidically linked building block β‐ D ‐Man p ‐(→4)‐α‐ D ‐Glc p NAc. The trichloroacetimidate method was particularly successful for synthesizing these glycosidic linkages.