Elsevier

Carbohydrate Research

Volume 238, 15 January 1993, Pages 93-107
Carbohydrate Research

Synthesis and immunoreactivity of poly(acrylamide) copolymers containing C-3- and C-7-modified, carboxyl-reduced, 4-O- and 5-O-phosphorylated K

https://doi.org/10.1016/0008-6215(93)87007-FGet rights and content

Abstract

Sodium (allyl 3-deoxy-α-d-lyxo-2-heptulopyranosid)onate (6), allyl 3-deoxy-β- and -α-d-manno-2-octulopyranoside, sodium (allyl 3-deoxy-β-l-gulo-2-octulopyranosid)onate, sodium (allyl α-d-glycero-d-talo-2-ocutulopyranosid)onate, sodium (allyl α-d-glycero-d-galacto -2-octulopyranosidonate, ammonium (allyl 3-deoxy-4-O- and -5-O-phosphono-α-d-manno-2-octulopyranosid)onate, and ammonium (allyl 3-deoxy-4-O- and -5-O-phosphono-β-d-manno-2-octulopyranosid)onate were prepared and copolymerized with acrylamide to give multivalent haptens, which were used in immune inhibition assays. The monoclonal antibody A 20, directed against α-pyranoside Kdo residues, did not react with these compounds, except with heptulosonic acid derivative 6, thus proving that the terminal hydroxymethyl group of Kdo is not required for binding.

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      Orthoester rearrangement in the presence of substoichiometric amounts of trimethylsilyl trifluoromethanesulfonate [16] furnished exclusively the α-allyl glycoside 14 (74%). Deprotection of 14 by Zemplén de-O-acylation and subsequent alkaline hydrolysis of the methyl ester gave the previously known sodium allyl d-glycero-α-d-talo-oct-2-ulopyranosidonate (15, 93%) [17]. Radical addition of cysteamine hydrochloride to the allyl group afforded the corresponding 3-(2-aminoethylthio)propyl glycoside 16 (65%).

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