Synthesis of pentasaccharide core structures corresponding to the genus-specific lipopolysaccharide epitope of Chlamydia.
The trisaccharides allyl O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->6)-O-2-aceta mid o-2-deoxy- beta-D-glucopyranosyl-(1-->6)-2-acetamido-2-deoxy-alpha- and -beta-D-glucopyranoside (16a and 16b), the tetrasaccharides allyl O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->4)-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->6)-O-2-aceta mid o-2-deoxy- beta-D-glucopyranosyl-(1-->6)-2-acetamido-2-deoxy-alpha- and -beta-D-glucopyranoside (19a and 19b), and the pentasaccharides allyl O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->8)-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->4)-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->6)-O-2-aceta mid o-2-deoxy-bet a -D-glucopyranosyl-(1-->6)-2-acetamido-2-deoxy-alpha- and -beta-D-glucopyranoside (23a and 23b) were prepared. The glycosidic linkages were formed using 1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-D-glucopy ran ose (6) and FeCl3 as promoter as well as per-O-acetylated Kdo mono- and di-saccharide bromide derivatives (12 and 20) under Helferich conditions. The oligosaccharides, which correspond to dephosphorylated part-structures of enterobacterial and chlamydial lipopolysaccharides, were characterized by NMR spectroscopy as well as plasma desorption and matrix-assisted laser desorption mass spectrometry.
Kosma
P
P
Institut für Chemie der Universität für Bodenkultur, Wien, Austria.
Strobl
M
M
Allmaier
G
G
Schmid
E
E
Brade
H
H
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002689:Chlamydia / Q000276:immunology*; D000939:Epitopes / Q000737:chemistry*; D007202:Indicators and Reagents; D008070:Lipopolysaccharides / Q000737:chemistry* / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D009904:Optical Rotation; D013329:Structure-Activity Relationship
D000939:Epitopes; D007202:Indicators and Reagents; D008070:Lipopolysaccharides; D009844:Oligosaccharides