176690-92-9Relevant academic research and scientific papers
Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose
Fettke, Anja,Peikow, Dirk,Peter, Martin G.,Kleinpeter, Erich
supporting information; experimental part, p. 4356 - 4366 (2009/10/09)
The synthesis of six analogs of N,N′-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molec
Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis
Berkin, Ali,Szarek, Walter A.,Kisilevsky, Robert
, p. 250 - 263 (2007/10/03)
4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [3H]GlcN and [35S]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-galactopyranose (31) exhibited a reduction of [3H]GlcN and [35S]SO4 incorporation to 1 and 9%, respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [14C]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. Copyright (C) 2000 Elsevier Science Ltd.
Stereoselective synthesis of N-acetyl thiochitooligosaccharides. Different behaviours of methyl N-acetyl-α- and -β-thiochitobiosides during acetolysis
Wang, Lai-Xi,Lee, Yuan C.
, p. 581 - 591 (2007/10/03)
A stereoselective synthesis of N-acetyl-thiochito-di-, -tri- and -tetra-saccharides is described. Coupling of methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-triflyl-β- 4 or -α-D-galactopyranoside 19 with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose 5 in the presence of cysteamine in DMF gave, after de-O-acylation, methyl N,N′-diacetyl-β- 9 and -α-thiochitobioside 21, respectively. Different behaviours of peracetylated methyl β- 10 and α-thiochitobioside 22 towards acetolysis with Ac2O-AcOH-H2SO4 solution were observed, with the β-isomer giving acyclic sugar species together with the desired thiochitobiose peracetate 11, while the α-isomer gave exclusively the thiochitobiose peracetate 11. This remarkable difference between α- and β-glycosides was further demonstrated by comparative acetolysis of methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α- 23 and -β-D-glucopyranoside 24. Methyl N,N′,N″-triacetylthiochitotriosides 29 and 30 were synthesized through conversion of N,N′-diacetylthiochitobiose peracetate 11 into N,N′-diacetyl-1,4-dithiochitobiose derivative 28, followed by its coupling with triflates 4 and 19 in the presence of cysteamine. Similarly, extension of the sugar chain to a higher homologue was achieved by converting methyl N,N′,N″-triacetylthiochitotrioside 30 into the N,N′,N″-triacetyl-1,4,4′-trithiochitotriose derivative 33, the coupling of which with triflate 19 in the presence of cysteamine provided the methyl N,N′,N″,N?-tetraacetylthiochitotetraoside 34 after de-O-acylation. Copyright 1996 by the Royal Society of Chemistry.
