A Sustainable One‐Pot, Two‐Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides | Zendy

Bassanini Ivan | Zendy; Krejzová Jana | Zendy; Panzeri Walter | Zendy; Monti Daniela | Zendy; Křen Vladimir | Zendy; Riva Sergio | Zendy

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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.

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