A novel zwitterionic HILIC stationary phase based on “thiol-ene” click chemistry between cysteine and vinyl silica

Abstract

A novel zwitterionic stationary phase with high hydrophilicity was facilely synthesized based on the "thiol-ene" click reaction between cysteine and vinyl silica, which exhibited great potential in the separation of oligosaccharides, peptides and basic compounds, as well as in the enrichment of glycopeptides.

Preparation and chromatographic evaluation of a cysteine-bonded zwitterionic hydrophilic interaction liquid chromatography stationary phase

“…As outlined in the comprehensive review by Ikegami et al [12], separation efficiency on HILIC columns was generally lower than that on RPLC columns. However, the Click TE-Cys column exhibited high separation efficiency in the separation of polar compounds, with the column efficiency as high as 72,000, 75,000 and 82,000 N/m for cytosine, cytidine and orotic acid, respectively [22]. In order to further investigate the chromatographic performance of the Click TE-Cys stationary phase, the kinetic evaluation of Click TE-Cys stationary phase was carried out by plotting the plate height (H, m) vs. linear velocity (u, mm s −1 , 1 mm s −1 corresponded to 0.65 mL min −1 ).…”

“…Unlike the typical zwitterionic stationary phases, the distribution of oppositely charged groups was paralleled to the surface of the silica gel. Besides, the Click TE-Cys stationary phase exhibited excellent hydrophilicity and great potential in the separation of polar compounds, as well as in the enrichment of glycopeptides [22]. In this study, the retention behaviors under HILIC mode were investigated in detail using a set of polar compounds to further characterize the chromatographic properties of Click TE-Cys stationary phase.…”

“…doi:10.1016/j.chroma.2011. 10.086 stationary phase [22] (designated Click TE-Cys, in which "Click TE" stands for "thiol-ene" click chemistry and "Cys" represents cysteine). The Click TE-Cys stationary phase belonged to zwitterionic stationary phases, with the surface charge switching slightly from positive to negative between pH 3 and 7.…”

Click aspartic acid as H ILIC SPE material for selective enrichment of N-linked glycopeptides

“…Preparation of novel HILIC materials is an important way to solve this issue. Recently we have developed several kinds of HILIC materials via click chemistry method [15][16][17][18][19][20]. Among them, Click maltose, Click OEG-CD and Click carboxylic acid (CA) were successfully used to enrich glycopeptides [15,18,19].…”

Development and evaluation of new imidazolium-based zwitterionic stationary phases for hydrophilic interaction chromatography

“…Therefore, the development of new stationary phases for HILIC has been the subject in recent years with the purpose of increasing the diversity of HILIC stationary phases to enlarge the coverage to polar and hydrophilic compounds. Recently, a new class of zwitterionic stationary phases for HILIC exhibited fairly good chromatographic behavior, including commercially available ZIC-HILIC and other reported zwitterionic stationary phases [3][4][5].…”