A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective "trimming" of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.

A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides / I. Bassanini, J. Krejzová, W. Panzeri, D. Monti, V. Křen, S. Riva. - In: CHEMSUSCHEM. - ISSN 1864-5631. - 10:9(2017 May 09), pp. 2040-2045. [10.1002/cssc.201700136]

A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides

I. Bassanini;S. Riva
2017-05-09

Abstract

A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective "trimming" of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.
enzyme catalysis; glycosylation; green chemistry; natural products; synthetic methods; Alcohols; Aspergillus niger; Biocatalysis; Glucosides; Glycoside Hydrolases; Glycosylation; Green Chemistry Technology; Rutin; Environmental Chemistry; Chemical Engineering (all); Materials Science (all); Energy (all)
Settore CHIM/06 - Chimica Organica
CHEMSUSCHEM
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/526254
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