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Bausteine von Oligosacchariden, CV. Synthese des Pentasaccharids L ‐α‐ D ‐Hep‐(1→3)‐ L ‐α‐ D ‐Hep‐(1→5)‐α‐Kdo‐(2→6)‐β‐ D ‐GlcNhm‐(1→6)‐ D ‐GlcNhm der linearen Core‐ und Lipoid‐A‐Struktur von Lipopolysacchariden
Author(s) -
Paulsen Hans,
Höffgen Elisabeth C.
Publication year - 1993
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.199319930188
Subject(s) - chemistry , stereochemistry , residue (chemistry) , trisaccharide , biochemistry
Building Units of Oligosaccharides, CV. – Synthesis of the Pentasaccharide L ‐α‐ D ‐Hep‐(1→3)‐ L ‐α‐ D ‐Hep‐(1→5)‐α‐Kdo‐(2→6)‐β‐ D ‐GlcNhm‐(1→6)‐ D ‐GlcNhm of the Linear Core and Lipoid A Structure of Lipopolysaccharides Using the trichloroacetimidate method we synthesized a trisaccharide donor containing the sequence L ‐α‐ D ‐Hep‐(1→3)‐ L ‐α‐ D ‐Hep‐(1→5)‐α‐Kdo. This block was coupled stereoselectively with a lipoid A analogue acceptor 22 , composed of two glucosamin units, giving the pentasaccharide 23 . After deblocking we obtained the pentasaccharide L ‐α‐ D ‐Hep‐(1→3)‐ L ‐α‐ D ‐Hep‐(1→5)‐α‐Kdo‐(2→6)‐β‐ D ‐GlcNhm‐(1→6)‐ D ‐GlcNhm ( 28 ), which represents the linear structure of the inner core and lipoid A chain of lipopolysaccharides. Sheep erythrocytes can be coated with compound 28 by incorporation of the fatty acids into the cell membrane. This complex presents the antigenic determinant composed of two heptose residues and one Kdo residue above the cell surface.