Green high-performance liquid chromatography enantioseparation of lansoprazole using a cellulose-based chiral stationary phase under ethanol/water mode

Abstract

A simple and environmentally friendly reversed-phase high-performance liquid chromatography method for the separation of the enantiomers of lansoprazole has been developed. The chromatographic resolution was carried out on the cellulose-based Chiralpak IC-3 chiral stationary phase using a green and low-toxicity ethanol-aqueous mode. The effects of water content in the mobile phase and column temperature on the retention of the enantiomers of lansoprazole and its chiral and achiral related substances have been carefully investigated. A mixed-mode hydrophilic interaction liquid chromatography and reversed-phase retention mechanism operating on the IC-3 chiral stationary phase allowed us to achieve simultaneous enantioselective and chemoselective separations in water-rich conditions. The enantiomers of lansoprazole were baseline resolved with a mobile phase consisting of ethanol/water 50:50 without any interference coming from chiral and achiral impurities within 10 min.

A chromatographic study on the retention behavior of the amylose tris(3‐chloro‐5‐methylphenylcarbamate) chiral stationary phase under aqueous conditions

“…The curves obtained by plotting the retention factors of both enantiomers versus the water content in the binary mobile phases are shown in Figure . In agreement with what already evidenced in correlated researches involving other polysaccharide‐based CSPs , the U‐shape retention plots obtained in ACN‐aqueous mode highlight two different regions, which are associated with two complementary retention mechanisms. On the left side of the U‐turn point, the decreasing zone is characterized by a water‐poor region (<40 vol) in which the water acts as the strongest eluting solvent.…”

“…The column temperature was set at 25 • C. The curves obtained by plotting the retention factors of both enantiomers versus the water content in the binary mobile phases are shown in Figure 1. In agreement with what already evidenced in correlated researches involving other polysaccharide-based CSPs [11][12][13][14][15], the U-shape retention plots obtained in ACN-aqueous mode highlight two different regions, which are associated with two complementary On the left side of the U-turn point, the decreasing zone is characterized by a water-poor region (<40 vol) in which the water acts as the strongest eluting solvent. Within this zone, which is commonly assigned to HILIC mode, any increase in water content in the mobile phase brings about a decrease in retention of both enantiomers of OXFZ.…”

“…[7] and Okamoto et al [8] on the HILIC-like behavior of polysaccharide-based CSPs are dated around two decades ago, there is a general tendency to classify as RP enantioseparation each enantioselective analysis carried out with organic-aqueous eluents. Actually, as highlighted just in a few works [9][10][11][12][13][14][15][16], the polysaccharide-based materials can behave T A B L E 1 Chromatographic results in polar organic conditions as classical RP-like CSPs, and at the same time as HILIC-like CSPs, depending on the content of water in mobile phase (i.e. under HILIC domain the content of water is usually lower than 40%).…”

Polysaccharide‐based chiral stationary phases as halogen bond acceptors: A novel strategy for detection of stereoselective σ‐hole bonds in solution

“…Envisaging, for polysaccharide derivatives, a novel function other than resolution of racemic mixtures , in this paper we show that HPLC coupled with polysaccharide‐based CSPs as XB acceptors (XBAs) can serve as analytical means for detection of weak stereoselective XBs in solution. Chiral halogenated 4,4′‐bipyridines lacking perfluorination were used as XBD test compounds.…”

State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013–2017)

“…It is well known that a single CSP cannot be universally used for chiral resolution of all racemic compounds. [40,41,[45][46][47][48][49][50][51]. In all these cases, the authors used reversed or normal phase modes.…”