Synthesis of poly(acrylamide) copolymers containing 3,5-dideoxy-d-arabino-2-octulopyranosylonic acid (5-deoxy-Kdo) residues

Kosma, Paul; Waldstätten, Peter; Daoud, Laurent; Schulz, Gerhard; Unger, Frank M.

doi:10.1016/0008-6215(89)85014-1

Cited by 11 publications

(2 citation statements)

References 26 publications

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“…), aKdo(2® 4)aKdo(2® allyl, aKo(2®4)aKdo(2®allyl and aKdo(2®4)aKo(2®allyl) were synthesized as described. [8][9][10][11][12][13] The allyl glycosides R-OCH 2 -CH=CH 2 were reacted with cysteamine 14 yielding R-O(CH 2 ) 3 -S-(CH 2 ) 2 -NH 3 + ligands (it is noted that conjugation was not achieved with Kdo-4P, 7epiKdo and Kdh), which were activated with thiophosgene into the isothiocyanate derivatives R-O(CH 2 ) 3 -S-(CH 2 ) 2 -N=C=S and then conjugated to bovine serum albumin (BSA) yielding R-O(CH 2 ) 3 -S-(CH 2 ) 2 -NH-CS-NH-BSA, where R represents the glycosyl residue. The latter compounds are abbreviated as R-BSA.…”

Section: Synthetic Oligosaccharides and Neoglycoconjugate Antigensmentioning

confidence: 99%

Monoclonal antibodies against 3-deoxy-α-D-manno-oct-2-ulosonic acid (Kdo) and D-glycero-α-D-talo-oct-2-ulosonic acid (Ko)

Brade

Gronow

Wimmer³

et al. 2002

Journal of Endotoxin Research

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Monoclonal antibodies (mAbs) were obtained after immunization of mice with neoglycoconjugates containing as a ligand the disaccharide Kdo(2-->4)Ko or Ko(2-->4)Kdo, representing structural elements of the core region of lipopolysaccharides (LPSs) from Acinetobacter haemolyticus and Burkholderia cepacia, respectively. One antibody, S67-9, bound with high specificity to Ko(2-->4)Kdo-BSA showing no cross reactivity with Kdo(2-->4)Kdo-BSA and the other antigens tested. A second mAb, S68-12, bound preferentially to Kdo(2-->4)Ko-BSA but cross reacted with Ko(2-->4)Kdo-BSA and Kdo(2-->4)Kdo-BSA. A third mAb, S67-27, was found to bind Kdo monosaccharide. Although mAbs S67-9 and S68-12 did not bind to LPS of Burkholderia or Acinetobacter as expected, the mAbs will be useful tools in studying the biosynthesis of LPS containing Ko.

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Section: Synthetic Oligosaccharides and Neoglycoconjugate Antigensmentioning

confidence: 99%

Monoclonal antibodies against 3-deoxy-α-D-manno-oct-2-ulosonic acid (Kdo) and D-glycero-α-D-talo-oct-2-ulosonic acid (Ko)

Brade

Gronow

Wimmer³

et al. 2002

Journal of Endotoxin Research

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“…A number of the previous glycopolymer syntheses relied on the copolymerization of ally! glycosides (7)(8)(9) and acrylamides. Most recently, we (10-13) and others (14,15) have modified the method using N-acryloylated carbohydrate monomers having lengthened spacer arms.…”

Section: Introductionmentioning

confidence: 99%

New strategy in glycopolymer syntheses. Preparation of antigenic water-soluble poly(acrylamide-co-p-acrylamidophenyl .beta.-lactoside)

Roy¹,

Tropper²,

Romanowska³

1992

Bioconjugate Chem.

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Stereospecific phase-transfer-catalyzed glycosidation of acetobromolactose 3 with p-nitrophenoxide gave the peracetylated 1,2-trans-beta-D-4-nitrophenyl lactoside 4. Functionalization of 4 into an N-acryloyl monomer was achieved by catalytic transfer hydrogenation of the nitro group, followed by N-acryloylation of the resulting amino group, on both O-acetyl-protected and unprotected disaccharides. Copolymerization of 4-acrylamidophenyl beta-lactoside (9) with acrylamide, initiated by ammonium persulfate, afforded a water-soluble carbohydrate copolymer (glycopolymer). The antigenicity of the new polymer was demonstrated by agar gel diffusion with Arachis hypogaea (peanut) and Ricinus communis (castor bean) lectins. Quantitative precipitation and enzyme linked lectin assays (ELLA) were also performed with peanut lectin.

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Bausteine von Oligosacchariden, XCVIII. Synthese von Oligosacchariden der inneren Core‐ und Lipoid‐A‐Region von Lipopolysacchariden

Paulsen

Brenken

1991

Liebigs Ann. Chem.

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Building Units of Oligosaccharides, XCVIII. – Synthesis of Oligosaccharides of the Inner Core and Lipoid A Region of Lipopolysaccharides Glycosidic coupling of the Hep‐Kdo disaccharide bromide 9 with the Lipoid A analogous disaccharide 10 gives the tetrasaccharide 11 which was deprotected to yield the tetrasaccharide L‐α‐D‐Hepp‐(1→5)‐α‐Kdop‐(2→6)‐β‐D‐GlcpNhm‐(1→6)‐D‐GlcNhm (18). In a further block synthesis 10 was glycosylated with the Hep‐[Kdo]‐Kdo donor 24. Deprotection of the corresponding pentasaccharide 25 furnished L‐α‐D‐Hepp‐(1→5)‐[α‐Kdop]‐(2→4)‐α‐Kdop‐(2→6)‐β‐D‐GlcpNhm‐(1→6)‐D‐GlcNhm (31). Sheep erythrocytes can be coated with these oligosaccharides 18 and 31. The resulting complexes are used as synthetic antigens and immunogens containing the disaccharide L‐α‐D‐Hepp‐(1→5)‐α‐Kdop and the branched trisaccharide L‐α‐D‐Hepp‐[α‐Kdop‐(2→4)]‐α‐Kdo as antigenic determinants.

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Synthesis of poly(acrylamide) copolymers containing 3,5-dideoxy-d-arabino-2-octulopyranosylonic acid (5-deoxy-Kdo) residues

Cited by 11 publications

References 26 publications

Monoclonal antibodies against 3-deoxy-α-D-manno-oct-2-ulosonic acid (Kdo) and D-glycero-α-D-talo-oct-2-ulosonic acid (Ko)

Monoclonal antibodies against 3-deoxy-α-D-manno-oct-2-ulosonic acid (Kdo) and D-glycero-α-D-talo-oct-2-ulosonic acid (Ko)

New strategy in glycopolymer syntheses. Preparation of antigenic water-soluble poly(acrylamide-co-p-acrylamidophenyl .beta.-lactoside)

Bausteine von Oligosacchariden, XCVIII. Synthese von Oligosacchariden der inneren Core‐ und Lipoid‐A‐Region von Lipopolysacchariden

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