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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todo:paper_09680896_v18_n14_p5339_Bordoni2023-10-03T15:55:13Z Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases Bordoni, A. De Lederkremer, R.M. Marino, C. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09680896_v18_n14_p5339_Bordoni |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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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 Bordoni, A. De Lederkremer, R.M. Marino, C. 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. |
| format |
JOUR |
| author |
Bordoni, A. De Lederkremer, R.M. Marino, C. |
| author_facet |
Bordoni, A. De Lederkremer, R.M. Marino, C. |
| author_sort |
Bordoni, A. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_09680896_v18_n14_p5339_Bordoni |
| work_keys_str_mv |
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