502435-18-9Relevant academic research and scientific papers
Total synthesis of LewisX using a late-stage crystalline intermediate
Munneke, Stefan,Painter, Gavin F.,Gainsford, Graeme J.,Stocker, Bridget L.,Timmer, Mattie S.M.
, p. 1 - 7 (2015)
Abstract Herein, we report on a highly efficient synthesis of a crystalline protected LewisX trisaccharide that was converted to LewisX following global deprotection. The trisaccharide was prepared in a highly convergent synthesis (seven steps, longest linear sequence) and in a 38% overall yield using a strategy that involved the regioselective glycosylation of a GlcNAc acceptor with a galactose thioglycoside donor, followed by fucosylation of the remaining free GlcNAc hydroxyl as key steps. The core trisaccharide also has the potential to be converted to other members of the Type-2 Lewis family of antigens due to the orthogonal nature of the protecting groups employed.
The effect of deoxyfluorination and: O -acylation on the cytotoxicity of N -acetyl-d-gluco- And d-galactosamine hemiacetals
Hamala, Vojtěch,?ervenková ??astná, Lucie,Kurfi?t, Martin,Cu?ínová, Petra,Balouch, Martin,Hrstka, Roman,Voňka, Petr,Karban, Jind?ich
supporting information, p. 4497 - 4506 (2021/05/31)
Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.
Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
Gallo-Rodriguez, Carola,Gil-Libarona, M.Agustina,Mendoza, Verónica M,De Lederkremer, Rosa M
, p. 9373 - 9380 (2007/10/03)
The synthesis of free β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-D-Galf-(1→4)-D-GlcNAc with a donor derivative of β-D-Galp-(1→3)-D-Galp. The trichloroacetimidate method, as well as SnCl4-promoted condensation were utilized for the introduction of the galactofuranosyl unit. On the other hand, the glycosyl-aldonolactone approach, followed by reduction of the lactone with diisoamylborane, and further isomerization to the galactopyranose configuration gave the donor derivative, which was condensed by the trichloroacetimidate method. Moreover, a synthon for the introduction of the β-D-Galp-(1→3)-D-Galf unit is described.
