Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase
Thiodisaccharides having β-d-Galf or α-l-Araf units as non-reducing end have been synthesized by the SnCl 4 - or MoO 2 Cl 2 -promoted thioglycosylation of per-O-benzoyl-d-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-α-l-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose de...
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v17_n7_p2703_Repetto http://hdl.handle.net/20.500.12110/paper_09680896_v17_n7_p2703_Repetto |
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paper:paper_09680896_v17_n7_p2703_Repetto2023-06-08T15:58:52Z Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase Repetto, Evangelina Marino, María Carla Uhrig, María Laura Varela, Oscar José Furanose Furanosidase inhibition Thiodisaccharides 1 o acetyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranoside 1 o acetyl derivative 1,2:3,4 di o isopropylidene 6 s (2,3,5,6 tetra o benzoyl dextro galactofuranosyl) 6 thio alpha dextro galactopyranose acetic acid derivative arabinofuranose beta dextro galactofuranosidase carbohydrate derivative disaccharide furan derivative galactofuranose methyl 2,3,4 tri o benzoyl 6 deoxy 6 thiocyano alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 o tosyl alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 6 s (arabinose arabinofuranosyl) 6 thio alpha glucopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside unclassified drug article carbohydrate synthesis enzyme activity enzyme inhibition enzyme synthesis glycosylation Michael addition Penicillium Penicillium fellutanum Arabinose Catalysis Chlorine Compounds Disaccharides Enzyme Inhibitors Galactose Glycoside Hydrolases Manganese Compounds Oxides Penicillium Sulfides Tin Compounds Penicillium fellutanum Thiodisaccharides having β-d-Galf or α-l-Araf units as non-reducing end have been synthesized by the SnCl 4 - or MoO 2 Cl 2 -promoted thioglycosylation of per-O-benzoyl-d-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-α-l-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure β-d-Galf(1→6)-6-thio-α-d-Glcp-OMe (5) or β-d-Galf(1→6)-6-thio-α-d-Galp-OMe (15) were obtained. The respective α-l-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, β-d-Galf(1→4)-4-thio-3-deoxy-α-l-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-β-d-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. © 2009 Elsevier Ltd. All rights reserved. Fil:Repetto, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Marino, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Laura Uhrig, M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2009 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v17_n7_p2703_Repetto http://hdl.handle.net/20.500.12110/paper_09680896_v17_n7_p2703_Repetto |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Furanose Furanosidase inhibition Thiodisaccharides 1 o acetyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranoside 1 o acetyl derivative 1,2:3,4 di o isopropylidene 6 s (2,3,5,6 tetra o benzoyl dextro galactofuranosyl) 6 thio alpha dextro galactopyranose acetic acid derivative arabinofuranose beta dextro galactofuranosidase carbohydrate derivative disaccharide furan derivative galactofuranose methyl 2,3,4 tri o benzoyl 6 deoxy 6 thiocyano alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 o tosyl alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 6 s (arabinose arabinofuranosyl) 6 thio alpha glucopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside unclassified drug article carbohydrate synthesis enzyme activity enzyme inhibition enzyme synthesis glycosylation Michael addition Penicillium Penicillium fellutanum Arabinose Catalysis Chlorine Compounds Disaccharides Enzyme Inhibitors Galactose Glycoside Hydrolases Manganese Compounds Oxides Penicillium Sulfides Tin Compounds Penicillium fellutanum |
| spellingShingle |
Furanose Furanosidase inhibition Thiodisaccharides 1 o acetyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranoside 1 o acetyl derivative 1,2:3,4 di o isopropylidene 6 s (2,3,5,6 tetra o benzoyl dextro galactofuranosyl) 6 thio alpha dextro galactopyranose acetic acid derivative arabinofuranose beta dextro galactofuranosidase carbohydrate derivative disaccharide furan derivative galactofuranose methyl 2,3,4 tri o benzoyl 6 deoxy 6 thiocyano alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 o tosyl alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 6 s (arabinose arabinofuranosyl) 6 thio alpha glucopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside unclassified drug article carbohydrate synthesis enzyme activity enzyme inhibition enzyme synthesis glycosylation Michael addition Penicillium Penicillium fellutanum Arabinose Catalysis Chlorine Compounds Disaccharides Enzyme Inhibitors Galactose Glycoside Hydrolases Manganese Compounds Oxides Penicillium Sulfides Tin Compounds Penicillium fellutanum Repetto, Evangelina Marino, María Carla Uhrig, María Laura Varela, Oscar José Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| topic_facet |
Furanose Furanosidase inhibition Thiodisaccharides 1 o acetyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranoside 1 o acetyl derivative 1,2:3,4 di o isopropylidene 6 s (2,3,5,6 tetra o benzoyl dextro galactofuranosyl) 6 thio alpha dextro galactopyranose acetic acid derivative arabinofuranose beta dextro galactofuranosidase carbohydrate derivative disaccharide furan derivative galactofuranose methyl 2,3,4 tri o benzoyl 6 deoxy 6 thiocyano alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 o tosyl alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside methyl 2,3,4 tri o benzoyl 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside methyl 6 s (arabinose arabinofuranosyl) 6 thio alpha glucopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside unclassified drug article carbohydrate synthesis enzyme activity enzyme inhibition enzyme synthesis glycosylation Michael addition Penicillium Penicillium fellutanum Arabinose Catalysis Chlorine Compounds Disaccharides Enzyme Inhibitors Galactose Glycoside Hydrolases Manganese Compounds Oxides Penicillium Sulfides Tin Compounds Penicillium fellutanum |
| description |
Thiodisaccharides having β-d-Galf or α-l-Araf units as non-reducing end have been synthesized by the SnCl 4 - or MoO 2 Cl 2 -promoted thioglycosylation of per-O-benzoyl-d-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-α-l-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure β-d-Galf(1→6)-6-thio-α-d-Glcp-OMe (5) or β-d-Galf(1→6)-6-thio-α-d-Galp-OMe (15) were obtained. The respective α-l-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, β-d-Galf(1→4)-4-thio-3-deoxy-α-l-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-β-d-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. © 2009 Elsevier Ltd. All rights reserved. |
| author |
Repetto, Evangelina Marino, María Carla Uhrig, María Laura Varela, Oscar José |
| author_facet |
Repetto, Evangelina Marino, María Carla Uhrig, María Laura Varela, Oscar José |
| author_sort |
Repetto, Evangelina |
| title |
Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| title_short |
Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| title_full |
Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| title_fullStr |
Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| title_full_unstemmed |
Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| title_sort |
thiodisaccharides with galactofuranose or arabinofuranose as terminal units: synthesis and inhibitory activity of an exo β-d-galactofuranosidase |
| publishDate |
2009 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v17_n7_p2703_Repetto http://hdl.handle.net/20.500.12110/paper_09680896_v17_n7_p2703_Repetto |
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1768543191792877568 |