Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase
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-t...
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todo:paper_14770520_v10_n44_p8884_Manzano2023-10-03T16:19:01Z Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase Manzano, V.E. Uhrig, M.L. Varela, O. 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 (K<inf>i</inf> = 95 μM). © 2012 The Royal Society of Chemistry. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14770520_v10_n44_p8884_Manzano |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
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 (K<inf>i</inf> = 95 μM). © 2012 The Royal Society of Chemistry. |
| format |
JOUR |
| author |
Manzano, V.E. Uhrig, M.L. Varela, O. |
| spellingShingle |
Manzano, V.E. Uhrig, M.L. Varela, O. Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase |
| author_facet |
Manzano, V.E. Uhrig, M.L. Varela, O. |
| author_sort |
Manzano, V.E. |
| title |
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase |
| title_short |
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase |
| title_full |
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase |
| title_fullStr |
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase |
| title_full_unstemmed |
Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase |
| title_sort |
convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. inhibitory activity of the glycomimetics against a β-galactosidase |
| url |
http://hdl.handle.net/20.500.12110/paper_14770520_v10_n44_p8884_Manzano |
| work_keys_str_mv |
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1807316367044509696 |