Premium
A Sustainable One‐Pot, Two‐Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides
Author(s) -
Bassanini Ivan,
Krejzová Jana,
Panzeri Walter,
Monti Daniela,
Křen Vladimir,
Riva Sergio
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700136
Subject(s) - chemistry , yield (engineering) , glycosyl , organic chemistry , rutin , silica gel , enzyme , flavonoid , catalysis , materials science , metallurgy , antioxidant
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.