Preparation and Evaluation of a Molecular Recognition Bionic Solid Phase Extraction Column for Separation of Glucosides

A molecular recognition bionic solid phase extraction (SPE) column for separation of glucosides has been prepared using a positively charged β‐glucosylamidine as the ligand in which a glycon moiety is connected via an N‐glycoside linkage. β‐Glucosylamidine, highly potent and selective inhibitors of β‐glycosidase, is immobilized through a one‐step synthesize procedure involving the addition of β‐glucosylamine and 2‐iminothiolane. HCl simultaneously to a matrix modified with maleimido groups via an appropriate spacer to give a molecular recognition absorbent for β‐glucosides. N‐octyl‐β‐D‐glucopyranoside and β‐D‐galactopyranoside or α‐D‐mannopyranoside was directly chromatographed through the bionic chromatographic column, resulting in a much stronger retention of β‐D‐glucopyranoside than β‐D‐galactopyranoside and α‐D‐mannopyranoside. The retained glucopyranoside could only be eluted by glucose solution. This indicates that the binding of the glucoside was of specific nature that corresponds to the glycon substrate specificity of the glucoside. The ease of preparation and the selective nature of the molecular recognition bionic chromatography should promise a large‐scale preparation of the molecular recognition adsorbent for the purification and removal of glucosides according to their glycon substrate specificity.