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Synthesis of polyacrylamide copolymers containing α-(2→4)-β-, β-(2→4)-β-, and β-(2→4)-α-linked O-(3-deoxy-d-manno-2-octulopyranosylonate)-(3-deoxy-d-manno-2-octulo-pyranosylono) (KDO) residues

✍ Scribed by Paul Kosma; Gerhard Schulz; Frank M. Unger

Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
642 KB
Volume
180
Category
Article
ISSN
0008-6215

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✦ Synopsis

Glycosylation of methyl (ally1 7,8-di-0-tert-butyldimethylsilyl-3-deoxy-/3-Dmanno-2-octulopyranosid)onate with methyl (4,5,7,8-tetra-0-acetyl-3-deoxy-a-omanno-2-octulopyranosyl bromide)onate under Helferich conditions gave a 3: 1 mixture of the corresponding (Y-and P-(2+4)-linked disaccharide derivatives in 58% yield. Separation and subsequent deprotection of the isomers afforded sodium 0-[sodium (3-deoxy-a-and -~-D-manno-2-octu~opyranosy~)onate]-(2~4)-(a~~y~ 3deoxy-/3-o-munno-2-octulopyranosid)onate. Similarly, the glycoside sodium O-[sodium (3-deoxy-~-o-munno-2-octulopyranosyl)onate]-(2~4)-(allyl 3-deoxy-a-omunno-2-octulopyranosid)onate was obtained by glycosylation of methyl (ally1 7,8-O-carbonyl-3-deoxy-cY-D-manno-2-octulopyranosid)onate, followed by removal of the protecting groups. Radical copolymerization of the ally1 glycosides with acrylamide afforded linear macromolecular antigens suitable for the determination of cpitope-specificities of monoclonal antibodies directed against the KDO-region of enterobacterial lipopolysaccharides.

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