Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases
Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron trans...
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2010
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n14_p5339_Bordoni http://hdl.handle.net/20.500.12110/paper_09680896_v18_n14_p5339_Bordoni |
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paper:paper_09680896_v18_n14_p5339_Bordoni2023-06-08T15:58:53Z Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases 5-Deoxy-d-galactofuranosides Galactofuranosidase inhibition Galactofuranosidase substrates PET deoxygenation 4 methylphenyl 1 thio beta dextro galactofuranoside 4 methylthiophenyl 5 deoxy alpha levo arabinohexofuranoside 4 nitrophenyl 5 deoxy alpha levo arabinohexofuranoside 5 deoxy alpha levo arabinohexofuranoside 5 deoxy beta dextro galactofuranose galacturonic acid per o acetyl 5 deoxy alpha,beta levo arabinohexofuranoside unclassified drug article electron transport enzyme activity enzyme synthesis protein binding Galactosides Glycoside Hydrolases Penicillium Substrate Specificity Penicillium fellutanum Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl 4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. © 2010 Elsevier Ltd. All rights reserved. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n14_p5339_Bordoni http://hdl.handle.net/20.500.12110/paper_09680896_v18_n14_p5339_Bordoni |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
5-Deoxy-d-galactofuranosides Galactofuranosidase inhibition Galactofuranosidase substrates PET deoxygenation 4 methylphenyl 1 thio beta dextro galactofuranoside 4 methylthiophenyl 5 deoxy alpha levo arabinohexofuranoside 4 nitrophenyl 5 deoxy alpha levo arabinohexofuranoside 5 deoxy alpha levo arabinohexofuranoside 5 deoxy beta dextro galactofuranose galacturonic acid per o acetyl 5 deoxy alpha,beta levo arabinohexofuranoside unclassified drug article electron transport enzyme activity enzyme synthesis protein binding Galactosides Glycoside Hydrolases Penicillium Substrate Specificity Penicillium fellutanum |
| spellingShingle |
5-Deoxy-d-galactofuranosides Galactofuranosidase inhibition Galactofuranosidase substrates PET deoxygenation 4 methylphenyl 1 thio beta dextro galactofuranoside 4 methylthiophenyl 5 deoxy alpha levo arabinohexofuranoside 4 nitrophenyl 5 deoxy alpha levo arabinohexofuranoside 5 deoxy alpha levo arabinohexofuranoside 5 deoxy beta dextro galactofuranose galacturonic acid per o acetyl 5 deoxy alpha,beta levo arabinohexofuranoside unclassified drug article electron transport enzyme activity enzyme synthesis protein binding Galactosides Glycoside Hydrolases Penicillium Substrate Specificity Penicillium fellutanum Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| topic_facet |
5-Deoxy-d-galactofuranosides Galactofuranosidase inhibition Galactofuranosidase substrates PET deoxygenation 4 methylphenyl 1 thio beta dextro galactofuranoside 4 methylthiophenyl 5 deoxy alpha levo arabinohexofuranoside 4 nitrophenyl 5 deoxy alpha levo arabinohexofuranoside 5 deoxy alpha levo arabinohexofuranoside 5 deoxy beta dextro galactofuranose galacturonic acid per o acetyl 5 deoxy alpha,beta levo arabinohexofuranoside unclassified drug article electron transport enzyme activity enzyme synthesis protein binding Galactosides Glycoside Hydrolases Penicillium Substrate Specificity Penicillium fellutanum |
| description |
Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl 4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. © 2010 Elsevier Ltd. All rights reserved. |
| title |
Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| title_short |
Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| title_full |
Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| title_fullStr |
Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| title_full_unstemmed |
Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| title_sort |
synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases |
| publishDate |
2010 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n14_p5339_Bordoni http://hdl.handle.net/20.500.12110/paper_09680896_v18_n14_p5339_Bordoni |
| _version_ |
1768542949935677440 |