Synthesis of glycuronamides of amino acids, constituents of microbial polysaccharides and their conversion into neoglycoconjugates of copolymer type

Abstract

Glycopyranosiduronic acids, amidically linked to amino acids (alanine, serine, threonine, and lysine) were prepared. O-tert-Butyl and N epsilon-tert-butyloxycarbonyl protected amino acid tert-butyl esters were used in ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate promoted condensation with 2-azidoethyl glycosides of glucuronic and galacturonic acid. Reduction of the azido-function followed by N-acryloylation and removal of blocking groups with trifluoroacetic acid gave the target monomers. These were converted into neoglycoconjugates of copolymer type, potentially useful for immunochemical studies.