Synthesis of glycuronamides of amino acids, constituents of microbial polysaccharides and their conversion into neoglycoconjugates of copolymer type.
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.
Chernyak
A Y
AY
N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences, Moscow, USSR.
Sharma
G V
GV
Kononov
L O
LO
Krishna
P R
PR
Rao
A V
AV
Kochetkov
N K
NK
D000577:Amides / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D016667:Bacterial Capsules / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D014574:Uronic Acids / Q000138:chemical synthesis*
D000577:Amides; D000596:Amino Acids; D006001:Glycoconjugates; D011108:Polymers; D014574:Uronic Acids