Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides
Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, α-deoxygenation of D-galactono-1,4-lactone was easi...
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2002
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2119_Chiocconi http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2119_Chiocconi |
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paper:paper_00086215_v337_n21-23_p2119_Chiocconi2023-06-08T14:32:42Z Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides Chiocconi, Alejandro Andrés Otal, Eugenio Hernán Muchnik de Lederkremer, Rosa María 2-Deoxy-D-lyxo- hexono-1,4-lactone 2-Deoxy-D-lyxo-hexofuranosides Deoxy sugars Exo β-D-Galactofuranosidase Electrons Enzymes Hydrolysis Photochemical reactions Sodium compounds Synthesis (chemical) Electron transfer Carbohydrates benzoic acid derivative carbohydrate derivative dextro galactono 1,4 lactone lactone derivative methyl 2 deoxy beta dextro lyxohexafuranoside sodium iodide unclassified drug article carbohydrate synthesis chemical reaction degradation electron transport hydrolysis oxygenation Penicillium photochemistry priority journal reduction beta-Galactosidase Chromatography, High Pressure Liquid Electrons Galactose Glycoside Hydrolases Magnetic Resonance Spectroscopy Penicillium Photochemistry Structure-Activity Relationship Sugar Acids Penicillium fellutanum Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, α-deoxygenation of D-galactono-1,4-lactone was easily achieved by photochemical electron transfer deoxygenation of HO-2 as the 3-(trifluoromethyl)benzoate. Methyl 2-deoxy-β-D-lyxo-hexafuranoside ('methyl 2-deoxy-β-D-galactofuranoside') was synthesized and tested as substrate for exo β-D-galactofuranosidase from Penicillium fellutanum. The reaction was followed by HPAEC, showing that methyl 2-deoxy-β-D-galactofuranoside was not hydrolyzed by incubation with the enzyme. Neither the 2-deoxy lactone, nor the 2-deoxy-β-D-galactofuranoside acted as inhibitors of the reaction with the 4-nitrophenyl β-D-galactofuranoside. The present and our previous results show that the hydroxyl groups at C-2, C-3 and C-6 of the galactofuranoside are essential for interaction with the exo β-D-galactofuranosidase. © 2002 Elsevier Science Ltd. All rights reserved. Fil:Chiocconi, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Otal, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2119_Chiocconi http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2119_Chiocconi |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
2-Deoxy-D-lyxo- hexono-1,4-lactone 2-Deoxy-D-lyxo-hexofuranosides Deoxy sugars Exo β-D-Galactofuranosidase Electrons Enzymes Hydrolysis Photochemical reactions Sodium compounds Synthesis (chemical) Electron transfer Carbohydrates benzoic acid derivative carbohydrate derivative dextro galactono 1,4 lactone lactone derivative methyl 2 deoxy beta dextro lyxohexafuranoside sodium iodide unclassified drug article carbohydrate synthesis chemical reaction degradation electron transport hydrolysis oxygenation Penicillium photochemistry priority journal reduction beta-Galactosidase Chromatography, High Pressure Liquid Electrons Galactose Glycoside Hydrolases Magnetic Resonance Spectroscopy Penicillium Photochemistry Structure-Activity Relationship Sugar Acids Penicillium fellutanum |
| spellingShingle |
2-Deoxy-D-lyxo- hexono-1,4-lactone 2-Deoxy-D-lyxo-hexofuranosides Deoxy sugars Exo β-D-Galactofuranosidase Electrons Enzymes Hydrolysis Photochemical reactions Sodium compounds Synthesis (chemical) Electron transfer Carbohydrates benzoic acid derivative carbohydrate derivative dextro galactono 1,4 lactone lactone derivative methyl 2 deoxy beta dextro lyxohexafuranoside sodium iodide unclassified drug article carbohydrate synthesis chemical reaction degradation electron transport hydrolysis oxygenation Penicillium photochemistry priority journal reduction beta-Galactosidase Chromatography, High Pressure Liquid Electrons Galactose Glycoside Hydrolases Magnetic Resonance Spectroscopy Penicillium Photochemistry Structure-Activity Relationship Sugar Acids Penicillium fellutanum Chiocconi, Alejandro Andrés Otal, Eugenio Hernán Muchnik de Lederkremer, Rosa María Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides |
| topic_facet |
2-Deoxy-D-lyxo- hexono-1,4-lactone 2-Deoxy-D-lyxo-hexofuranosides Deoxy sugars Exo β-D-Galactofuranosidase Electrons Enzymes Hydrolysis Photochemical reactions Sodium compounds Synthesis (chemical) Electron transfer Carbohydrates benzoic acid derivative carbohydrate derivative dextro galactono 1,4 lactone lactone derivative methyl 2 deoxy beta dextro lyxohexafuranoside sodium iodide unclassified drug article carbohydrate synthesis chemical reaction degradation electron transport hydrolysis oxygenation Penicillium photochemistry priority journal reduction beta-Galactosidase Chromatography, High Pressure Liquid Electrons Galactose Glycoside Hydrolases Magnetic Resonance Spectroscopy Penicillium Photochemistry Structure-Activity Relationship Sugar Acids Penicillium fellutanum |
| description |
Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, α-deoxygenation of D-galactono-1,4-lactone was easily achieved by photochemical electron transfer deoxygenation of HO-2 as the 3-(trifluoromethyl)benzoate. Methyl 2-deoxy-β-D-lyxo-hexafuranoside ('methyl 2-deoxy-β-D-galactofuranoside') was synthesized and tested as substrate for exo β-D-galactofuranosidase from Penicillium fellutanum. The reaction was followed by HPAEC, showing that methyl 2-deoxy-β-D-galactofuranoside was not hydrolyzed by incubation with the enzyme. Neither the 2-deoxy lactone, nor the 2-deoxy-β-D-galactofuranoside acted as inhibitors of the reaction with the 4-nitrophenyl β-D-galactofuranoside. The present and our previous results show that the hydroxyl groups at C-2, C-3 and C-6 of the galactofuranoside are essential for interaction with the exo β-D-galactofuranosidase. © 2002 Elsevier Science Ltd. All rights reserved. |
| author |
Chiocconi, Alejandro Andrés Otal, Eugenio Hernán Muchnik de Lederkremer, Rosa María |
| author_facet |
Chiocconi, Alejandro Andrés Otal, Eugenio Hernán Muchnik de Lederkremer, Rosa María |
| author_sort |
Chiocconi, Alejandro Andrés |
| title |
Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides |
| title_short |
Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides |
| title_full |
Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides |
| title_fullStr |
Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides |
| title_full_unstemmed |
Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides |
| title_sort |
photoinduced electron transfer and chemical α-deoxygenation of d-galactono-1,4-lactone. synthesis of 2-deoxy-d-lyxo-hexofuranosides |
| publishDate |
2002 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2119_Chiocconi http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2119_Chiocconi |
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