title: A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides.
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.
authors.affiliation: Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, Milano, 20131, Italy.|Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milano, 20133, Italy.
authors.forename: Ivan
authors.initials: I
authors.lastname: Bassanini
authors.affiliation: Institute of Microbiology, Laboratory of Biotransformation, Czech Academy of Science, Vídeňská 1083, CZ, 142 20, Prague, Czech Republic.
authors.forename: Jana
authors.initials: J
authors.lastname: Krejzová
authors.affiliation: Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, Milano, 20131, Italy.|Dipartimento di Chimica, Materiali ed Ingegneria Chimica 'Giulio Natta', Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano, 20133, Italy.
authors.forename: Walter
authors.initials: W
authors.lastname: Panzeri
authors.affiliation: Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, Milano, 20131, Italy.
authors.forename: Daniela
authors.initials: D
authors.lastname: Monti
authors.affiliation: Institute of Microbiology, Laboratory of Biotransformation, Czech Academy of Science, Vídeňská 1083, CZ, 142 20, Prague, Czech Republic.
authors.forename: Vladimir
authors.initials: V
authors.lastname: Křen
authors.affiliation: Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, Milano, 20131, Italy.
authors.forename: Sergio
authors.initials: S
authors.lastname: Riva
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001234:Aspergillus niger / Q000201:enzymology; D055162:Biocatalysis; D005960:Glucosides / Q000138:chemical synthesis*; D006026:Glycoside Hydrolases / Q000378:metabolism; D006031:Glycosylation; D055772:Green Chemistry Technology; D012431:Rutin / Q000737:chemistry
chemical_list: D000438:Alcohols; D005960:Glucosides; D012431:Rutin; D006026:Glycoside Hydrolases; C022525:alpha-L-rhamnosidase
keywords: enzyme catalysis; glycosylation; green chemistry; natural products; synthetic methods