GLYCOPOLYMERS FROM SYNTHETIC FRAGMENTS (AMIDES OF ALPHA-D-GALACTURONIC ACID WITH AMINO-ACIDS) OF PROTEUS O-ANTIGENS

Galacturonamides of amino acids (alanine, lysine, serine, and threonine), constituents of Proteus O-specific polysaccharides, have been synthesised. O-tert-Butyl and N-epsilon-tert-butyloxycarbonyl protected amino acid tert-butyl esters were condensed with the 2-azidoethyl alpha-glycoside of D-galacturonic acid, prepared by Fischer glycosidation. Reduction of the azido group followed by N-acryloylation and deprotection gave the target monomers. By copolymerisation with acryl-amide, these were converted into glycopolymers potentially useful for defining epitopes in Proteus O-antigens.