Issue 15, 2020

Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation

Abstract

The disaccharide sucrose (α-D-glucopyranosyl-1,2-β-D-fructofuranoside) is a highly efficient donor substrate for enzymatic glucosylation reactions. A large number of commercially relevant glucosides are produced via this general route. Every sucrose-based glucosylation involves co-production of D-fructose in amounts corresponding to the target glucoside. A separation technology for selective removal, and efficient recovery, of the D-fructose co-product would be highly desirable as a generic platform for downstream process development. Here, we demonstrate organoboronate-complex reactive extraction of D-fructose into an 1-octanol/hexane (4/1, v/v) solvent using methyltrioctyl ammonium chloride as phase transfer catalyst and extractant. We show separation of the D-fructose co-product (100 mM) from equimolar mixture with 2-α-D-glucosyl-glycerol, a cosmetic ingredient that is manufactured industrially from sucrose and glycerol using sucrose phosphorylase. With the main parameters of extraction, stripping and organic phase recycling identified and their effect on product/co-product yield and purity characterized, we developed a three-step extraction process with alternating extraction and stripping stages that removed the D-fructose efficiently at 50 ml operating scale. 2-α-D-glucosyl-glycerol and D-fructose were cleanly separated and obtained in excellent purity (≥90%) at a recovery of 90% and 83%, respectively. Reactive extraction appears to be faster and more selective and resource-efficient than applicable alternatives for separation, including chromatography and membrane nanofiltration. Thus, the established extraction process is promising for industrial application. It could be generically useful to separate D-fructose from glucosides.

Graphical abstract: Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation

Supplementary files

Article information

Article type
Paper
Submitted
22 Apr 2020
Accepted
30 Jun 2020
First published
30 Jun 2020
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2020,22, 4985-4994

Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation

A. Kruschitz and B. Nidetzky, Green Chem., 2020, 22, 4985 DOI: 10.1039/D0GC01408G

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