592533-33-0Relevant academic research and scientific papers
Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases
Busca, Patricia,Piller, Veronique,Piller, Friedrich,Martin, Olivier R.
, p. 1853 - 1856 (2007/10/03)
A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-α-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity.
Synthesis of O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1 → 3)-2- acetamido-2-deoxy-4-O-sulfo-D-galactopyranose trisodium salt, a disaccharide fragment of dermatan sulfate
Rochepeau-Jobron, Laurence,Jacquinet, Jean-Claude
, p. 181 - 191 (2007/10/03)
Benzyl 2-acetamido-2-deoxy-α, and β-D-glucopyranoside were converted in high yield into the corresponding D-galacto analogues through a three- step procedure. These later were transformed in a straightforward manner into benzyl 2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-α, and β-D- galactopyranoside, respectively, which served as acceptors in glycosylation reactions with variously activated derivatives of methyl 2-O-benzoyl-3,O- benzyl-4-O-chloro-acetyl-L-idopyranuronate. Condensation of the chloride derivative promoted by silver triflate led unexpectedly to the formation of the β-linked disaccharide, whereas the trichloroacetimidoyl derivative afforded the expected α-linked disaccharide in 63% yield. O- Dechloroacetylation of this later, followed by 4-methoxybenzylation at O-4 of the uronic acid moiety, saponification of the esters, O-sulfonation of the free hydroxyls, and catalytic hydrogenation provided the title disaccharide in high yield, as its sodium salt.
