889453-93-4Relevant academic research and scientific papers
Zwitterionic Polysaccharides of Shigella sonnei: Synthetic Study toward a Ready-for-Oligomerization Building Block Made of Two Rare Amino Sugars
Pfister, Hélène B.,Paoletti, Julie,Poveda, Ana,Jimenez-Barbero, Jesus,Mulard, Laurence A.
, p. 4270 - 4282 (2018/11/23)
Shigellosis is an endemic diarrheal disease caused by Gram negative bacteria named Shigella. The most exposed polysaccharides of Shigella sonnei display a zwitterionic disaccharide repeating unit (AB) made of two rare amino sugars: [4)-α- l -Alt p NAcA-(1→3)-β- d -Fuc p NAc4N-(1→]. An original synthesis of a ready-for-oligomerization AB disaccharide is reported. The targeted orthogonally protected disaccharide was synthesized from l -glucose and tetra- O -acetyl-β- d -glucosamine. The challenging introduction of the 4 B -azido group masking the amino moiety of the AAT residue was performed at the disaccharide stage by a two-step procedure (triflation followed by nucleoaphilic displacement with NaN 3). A post-glycosylation oxidation strategy was employed to access the altruronate moiety.
Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
Wang, Peng,Wang, Jun,Guo, TianTian,Li, Yingxia
experimental part, p. 607 - 620 (2010/09/20)
Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by
