Chromatographic purification of enzymatically synthesized alkyl glucopyranosides

BACKGROUND Enzymatic synthesis and chromatographic purification of ethyl β‐D‐glucopyranoside was investigated. Ethyl β‐D‐glucopyranoside was produced from glucose and ethanol with β‐glucosidase enzyme ( EC 3.2.1.21). Cation exchange resins in Ca 2+ and Na + forms were used for the purification of ethyl‐β‐D‐glucopyranoside. RESULTS Greater than 60% conversion was obtained in the synthesis. The reaction which follows the double displacement mechanism was successfully modelled with a simple kinetic model. Good separation of ethyl‐β‐D‐glucopyranoside and glucose was obtained with weak acid cation exchange resins in Na + form. 5.5 wt% crosslinked resin performed slightly better than 8 wt% crosslinked resin. The separation is based on hydrophobic interactions. Presence of ethanol disturbs the separation and should be removed before the chromatographic step. Scale‐up of the purification step (bed volume: 0.11 L to 1.9 L) was successfully carried out to produce ethyl‐β‐D‐glucopyranoside with 99% purity. Performance of the purification process was evaluated with numerical simulations. With respect to ethyl‐β‐D‐glucopyranoside, the separation performance was found to go through a shallow maximum with increasing column loading and flow rate. CONCLUSION An efficient chromatographic purification method was developed for enzymatically produced ethyl‐β‐D‐glucopyranoside. This method could be utilized also in the purification of other enzymatically produced glucopyranosides. © 2015 Society of Chemical Industry