73962-00-2Relevant academic research and scientific papers
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase
Manzano, Veronica E.,Uhrig, Maria Laura,Varela, Oscar
, p. 8884 - 8894,11 (2012/12/13)
The ring-opening reaction of sugar 3,4-epoxides by 2,3,4,6-tetra-O-acetyl- 1-thio-β-d-galactopyranose (7) as a nucleophile led to (1 → 3)- and (1 → 4)-thiodisaccharides. High regio- and diastereoselectivities were achieved in the synthesis of the per-O-acetyl derivative of the β-d-Galp-S-(1 → 4)-4-thio-α-d-Glcp-O-iPr (10). Analogues of the 4-thiolactoside 10 have been prepared, with the β-d-Galp non-reducing end S-linked to d-Glcp, d-Gulp and d-Idop. A similar regioselective attack of 7 on C-4 of 2-propyl 3,6-di-O-acetyl-3,4-epithio-α-d-galactopyranoside (6) led to 2-propyl 3,4-dithiolactoside derivative 15. During this reaction the free 3-SH group of 15 underwent oxidative dimerization or oxidative coupling with the SH function of 7 to give the respective disulfides. Glycosylation of the thiol group of 15 using trichloroacetimidate derivatives of β-d-Galp or β-d-Galf afforded the corresponding branched dithiotrisaccharides. The free compounds were evaluated as inhibitors of the E. coli β-galactoside. The bis(2-propyl 3,4-dithiolactosid-3-yl)-disulfide, obtained from 15, displayed the strongest inhibitory activity in these series of glycomimetics and proved to be a non-competitive inhibitor (Ki = 95 μM). This journal is
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase
Manzano, Verónica E.,Uhrig, María Laura,Varela, Oscar
, p. 8884 - 8894 (2013/01/15)
The ring-opening reaction of sugar 3,4-epoxides by 2,3,4,6-tetra-O-acetyl- 1-thio-β-d-galactopyranose (7) as a nucleophile led to (1 → 3)- and (1 → 4)-thiodisaccharides. High regio- and diastereoselectivities were achieved in the synthesis of the per-O-acetyl derivative of the β-d-Galp-S-(1 → 4)-4-thio-α-d-Glcp-O-iPr (10). Analogues of the 4-thiolactoside 10 have been prepared, with the β-d-Galp non-reducing end S-linked to d-Glcp, d-Gulp and d-Idop. A similar regioselective attack of 7 on C-4 of 2-propyl 3,6-di-O-acetyl-3,4-epithio-α-d-galactopyranoside (6) led to 2-propyl 3,4-dithiolactoside derivative 15. During this reaction the free 3-SH group of 15 underwent oxidative dimerization or oxidative coupling with the SH function of 7 to give the respective disulfides. Glycosylation of the thiol group of 15 using trichloroacetimidate derivatives of β-d-Galp or β-d-Galf afforded the corresponding branched dithiotrisaccharides. The free compounds were evaluated as inhibitors of the E. coli β-galactoside. The bis(2-propyl 3,4-dithiolactosid-3-yl)-disulfide, obtained from 15, displayed the strongest inhibitory activity in these series of glycomimetics and proved to be a non-competitive inhibitor (Ki = 95 μM).
A general strategy toward S-linked glycopeptides
Thayer, Desiree A.,Yu, Henry N.,Galan, M. Carmen,Wong, Chi-Huey
, p. 4596 - 4599 (2007/10/03)
(Chemical Equation Presented) A high-yield one-pot synthesis of S-linked glycosyl amino acids 1 has been developed (see scheme; DMF = dimethyl formamide) and used in the solid-phase synthesis of S-linked glycopeptides. This approach has been shown to be efficient for the synthesis of various S-linked glycosyl amino acid building blocks.
Synthesis of cerebroside, lactosyl ceramide, and ganglioside GM3 analogs containing β-thioglycosidically linked ceramide
Hasegawa,Morita,Kojima,Ishida,Kiso
, p. 43 - 53 (2007/10/02)
Coupling of the sodium salt of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose, -β-D-galactopyranose, O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O- acetyl-1-thio-β-D-glucopyranose, or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto -2-nonulopyranosylonate)-(2→3)-O-(2,3-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-3-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D- glucopyranose, which were prepared from the corresponding 1-S-acetates, 1, 3, 6, and 9, with (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene- 1,3-diol (12) derived by tosylation of 11, gave the corresponding β-thioglycosides 13, 17, 21, and 25, respectively in good yield. The β-thioglycosides obtained were converted, via selective reduction of the azide group, condensation with octadecanoic acid, and removal of the protecting groups, into the title compounds. Coupling of the sodium salt of 2,3,4,6-tetra-O- acetyl-1-thio-β-D-glucopyranose, -β-D-galactopyranose, O-(2,3,4,6-tetra- O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3, 6-tri-O-acetyl-1-thio- β-D-glucopyranose, or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3, 5-dideoxy-D-glycero-α- D-galacto-2-nonulopyranosyl-onate)-(2→3) -O-(2,3-di-O-acetyl -6-O-bezoyl-β-D-galactopyranosyl) -(1→4) -3-O-acetyl-2,6-di-O- benzoyl-1-thio-β-D-glucopyranose, which were prepared from the corresponding 1-S-acetates, 1, 3, 6, and 9, with ( 2S,3R,4E)-2-azido-3 -O-benzoyl-1-O-(p-tolylsulfonyl) -4-octadecene-1,3 -diol (12) derived by tosylation of 11, gave the corresponding β-thioglycosides 13, 17, 21, and 25, respectively in good yield. The β-thioglycosides obtained were converted, via selective reduction of the azide group, condensation with octadecanoic acid, and removal of the protecting groups, into the title compounds.
