Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl...
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2012
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v347_n1_p69_Mazzaferro http://hdl.handle.net/20.500.12110/paper_00086215_v347_n1_p69_Mazzaferro |
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paper:paper_00086215_v347_n1_p69_Mazzaferro2023-06-08T14:33:01Z Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside Acremonium sp. DSM 24697 Diglycosidase Hesperidin Zymogram Acremonium Agitated reactors Aglycones Aromatic alcohols Diglycosidase Fluorogenic substrate Glucosidase Hesperidin Immobilized biocatalysts MALDI-TOF/TOF Monoisotopic mass One step Silica-gel chromatography Sugar acceptors Transglycosylation Zymogram Glucose Silica Silica gel Solvent extraction Glycosylation 4 methylumbelliferylrutinoside aglycone alpha rhamnosyl beta glucosidase dimethyl sulfoxide flavonoid glucose glucosidase hesperidin hymecromone unclassified drug Acremonium article biocatalyst controlled study correlation analysis enzyme activity enzyme specificity glycosylation hydrolysis isolation procedure matrix assisted laser desorption ionization time of flight mass spectrometry priority journal purification solvent extraction staining substitution reaction synthesis zymography Acremonium Disaccharides Fluorescent Dyes Glucosidases Glycosides Glycosylation Hymecromone Solubility Solvents Substrate Specificity Water Acremonium sp. Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na] + ions correlated with the theoretical monoisotopic mass (calcd [M+Na] +: 507.44 m/z; obs. [M+Na] +: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis. © 2011 Elsevier Ltd. All rights reserved. 30. 2012 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v347_n1_p69_Mazzaferro http://hdl.handle.net/20.500.12110/paper_00086215_v347_n1_p69_Mazzaferro |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Acremonium sp. DSM 24697 Diglycosidase Hesperidin Zymogram Acremonium Agitated reactors Aglycones Aromatic alcohols Diglycosidase Fluorogenic substrate Glucosidase Hesperidin Immobilized biocatalysts MALDI-TOF/TOF Monoisotopic mass One step Silica-gel chromatography Sugar acceptors Transglycosylation Zymogram Glucose Silica Silica gel Solvent extraction Glycosylation 4 methylumbelliferylrutinoside aglycone alpha rhamnosyl beta glucosidase dimethyl sulfoxide flavonoid glucose glucosidase hesperidin hymecromone unclassified drug Acremonium article biocatalyst controlled study correlation analysis enzyme activity enzyme specificity glycosylation hydrolysis isolation procedure matrix assisted laser desorption ionization time of flight mass spectrometry priority journal purification solvent extraction staining substitution reaction synthesis zymography Acremonium Disaccharides Fluorescent Dyes Glucosidases Glycosides Glycosylation Hymecromone Solubility Solvents Substrate Specificity Water Acremonium sp. |
| spellingShingle |
Acremonium sp. DSM 24697 Diglycosidase Hesperidin Zymogram Acremonium Agitated reactors Aglycones Aromatic alcohols Diglycosidase Fluorogenic substrate Glucosidase Hesperidin Immobilized biocatalysts MALDI-TOF/TOF Monoisotopic mass One step Silica-gel chromatography Sugar acceptors Transglycosylation Zymogram Glucose Silica Silica gel Solvent extraction Glycosylation 4 methylumbelliferylrutinoside aglycone alpha rhamnosyl beta glucosidase dimethyl sulfoxide flavonoid glucose glucosidase hesperidin hymecromone unclassified drug Acremonium article biocatalyst controlled study correlation analysis enzyme activity enzyme specificity glycosylation hydrolysis isolation procedure matrix assisted laser desorption ionization time of flight mass spectrometry priority journal purification solvent extraction staining substitution reaction synthesis zymography Acremonium Disaccharides Fluorescent Dyes Glucosidases Glycosides Glycosylation Hymecromone Solubility Solvents Substrate Specificity Water Acremonium sp. Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| topic_facet |
Acremonium sp. DSM 24697 Diglycosidase Hesperidin Zymogram Acremonium Agitated reactors Aglycones Aromatic alcohols Diglycosidase Fluorogenic substrate Glucosidase Hesperidin Immobilized biocatalysts MALDI-TOF/TOF Monoisotopic mass One step Silica-gel chromatography Sugar acceptors Transglycosylation Zymogram Glucose Silica Silica gel Solvent extraction Glycosylation 4 methylumbelliferylrutinoside aglycone alpha rhamnosyl beta glucosidase dimethyl sulfoxide flavonoid glucose glucosidase hesperidin hymecromone unclassified drug Acremonium article biocatalyst controlled study correlation analysis enzyme activity enzyme specificity glycosylation hydrolysis isolation procedure matrix assisted laser desorption ionization time of flight mass spectrometry priority journal purification solvent extraction staining substitution reaction synthesis zymography Acremonium Disaccharides Fluorescent Dyes Glucosidases Glycosides Glycosylation Hymecromone Solubility Solvents Substrate Specificity Water Acremonium sp. |
| description |
Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na] + ions correlated with the theoretical monoisotopic mass (calcd [M+Na] +: 507.44 m/z; obs. [M+Na] +: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis. © 2011 Elsevier Ltd. All rights reserved. 30. |
| title |
Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| title_short |
Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| title_full |
Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| title_fullStr |
Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| title_full_unstemmed |
Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| title_sort |
transglycosylation specificity of acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside |
| publishDate |
2012 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v347_n1_p69_Mazzaferro http://hdl.handle.net/20.500.12110/paper_00086215_v347_n1_p69_Mazzaferro |
| _version_ |
1768545216231374848 |