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Abstract:

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.

Registro:

Documento: Artículo
Título:Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
Autor:Mazzaferro, L.S.; Piñuel, L.; Erra-Balsells, R.; Giudicessi, S.L.; Breccia, J.D.
Filiación:INCITAP-CONICET (Consejo Nacional de Investigaciones Científicas y Técnicas), Departamento de Química, Universidad Nacional de la Pampa (UNLPam), Av. Uruguay 151, 6300 Santa Rosa, La Pampa, Argentina
CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón II, 3(er) P., 1428 Buenos Aires, Argentina
Palabras clave: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.
Año:2012
Volumen:347
Número:1
Página de inicio:69
Página de fin:75
DOI: http://dx.doi.org/10.1016/j.carres.2011.11.008
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:dimethyl sulfoxide, 67-68-5; glucose, 50-99-7, 84778-64-3; glucosidase, 9033-06-1; hesperidin, 520-26-3; hymecromone, 90-33-5; 4-methylumbelliferyl-rutinoside; Disaccharides; Fluorescent Dyes; Glucosidases, 3.2.1.-; Glycosides; Hymecromone, 90-33-5; Solvents; Water, 7732-18-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v347_n1_p69_Mazzaferro

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Citas:

---------- APA ----------
Mazzaferro, L.S., Piñuel, L., Erra-Balsells, R., Giudicessi, S.L. & Breccia, J.D. (2012) . Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside. Carbohydrate Research, 347(1), 69-75.
http://dx.doi.org/10.1016/j.carres.2011.11.008
---------- CHICAGO ----------
Mazzaferro, L.S., Piñuel, L., Erra-Balsells, R., Giudicessi, S.L., Breccia, J.D. "Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside" . Carbohydrate Research 347, no. 1 (2012) : 69-75.
http://dx.doi.org/10.1016/j.carres.2011.11.008
---------- MLA ----------
Mazzaferro, L.S., Piñuel, L., Erra-Balsells, R., Giudicessi, S.L., Breccia, J.D. "Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside" . Carbohydrate Research, vol. 347, no. 1, 2012, pp. 69-75.
http://dx.doi.org/10.1016/j.carres.2011.11.008
---------- VANCOUVER ----------
Mazzaferro, L.S., Piñuel, L., Erra-Balsells, R., Giudicessi, S.L., Breccia, J.D. Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside. Carbohydr. Res. 2012;347(1):69-75.
http://dx.doi.org/10.1016/j.carres.2011.11.008