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
1988; Elsevier BV; Volume: 180; Issue: 1 Linguagem: Inglês
10.1016/0008-6215(88)80059-4
ISSN1873-426X
AutoresPaul Kosma, Gerhard Schulz, Frank M. Unger,
Tópico(s)Proteoglycans and glycosaminoglycans research
ResumoGlycosylation of methyl (allyl 7,8-di-O-tert-butyldimethylsilyl-3-deoxy-β-d-manno-2-octulopyranosid)onate with methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-d-manno-2-octulopyranosyl bromide)onate under Helferich conditions gave a 3:1 mixture of the corresponding α- and β-(2→4)-linked disaccharide derivatives in 58% yield. Separation and subsequent deprotection of the isomers afforded sodium O-[sodium (3-deoxy-α- and -β-d-manno-2-octulopyranosyl)onate]-(2→4)-(allyl 3-deoxy-β-d-manno-2-octulopyranosid)onate. Similarly, the glycoside sodium O-[sodium (3-deoxy-β-d-manno-2-octulopyranosyl)onate]-(2→4)-(allyl 3-deoxy-α-d-manno-2-octulopyranosid)onate was obtained by glycosylation of methyl (allyl 7,8-O-carbonyl-3-deoxy-α-d-manno-2-octulopyranosid)onate, followed by removal of the protecting groups. Radical copolymerization of the allyl glycosides with acrylamide afforded linear macromolecular antigens suitable for the determination of epitope-specificities of monoclonal antibodies directed against the KDO-region of enterobacterial lipopolysaccharides.
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