321549-84-2Relevant academic research and scientific papers
Synthesis of neoglycoproteins containing D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko) ligands corresponding to core units from Burkholderia and Acinetobacter lipopolysaccharide
Wimmer, Norbert,Brade, Helmut,Kosma, Paul
, p. 549 - 560 (2007/10/03)
Glycal esters of Kdo derivatives were converted into 2,3-anhydro intermediates, which were transformed into D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko), as well as 3-O- and 4-O-p-nitrobenzoyl-Ko derivatives. The exo-allyl orthoester derivative, methyl {5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-2,3-O-[(1-exo-allyloxy)-ethylide ne]-D-glycero-β-D-talo-oct-2-ulopyranos}onate, prepared from the 4-O-pNBz-protected Ko derivative, was elaborated into the α-Ko allyl ketoside, the reducing disaccharide α-Kdop-(2→4)-Ko and the disaccharide α-Kdop-(2→4)-Kop-(2→OAll). Conversely, methyl[4,5,7,8-tetra-O-acetyl-3-O-(4-nitrobenzoyl)-α-D-glycero-D-talo-2-o ctulopyranosyl bromide]onate [Carbohydr. Res., 244 (1993) 69-84], was coupled with a Kdo acceptor to give the disaccharide α-Kop-(2→4)-Kdop-(2→OAll) after orthoester rearrangement and deprotection. The allyl glycosides were treated with cysteamine and converted into neoglycoproteins. The ligands correspond to inner core units from Acinetobacter haemolyticus and Burkholderia cepacia lipopolysaccharides. (C) 2000 Elsevier Science Ltd.
