Preparation and chromatographic properties of a multimodal chiral stationary phase based on phenyl‐carbamate‐propyl‐β‐CD for HPLC

Abstract

A phenylcarbamate derivative of 2-hydroxypropyl-beta-CD bonded stationary phase was prepared by a previously described method. Its enantiomeric recognition abilities were evaluated as chiral stationary phase (CSP) in normal, polar organic and RP conditions by HPLC. The relevant structural features of the prepared stationary phase which make it an effective chiral selector are discussed. This material seems to have an excellent enantioselectivity for a variety of racemic analytes in the three modes. Hence it can be considered a highly effective multimodal column. Retention factor (k), selectivity (alpha) and resolution (R(s)) were the chosen parameters to describe the column performance. Optimization of these separations was discussed in terms of mobile phase composition, flow rate and structural patterns of the injected analytes.

Analysis of hesperetin enantiomers in human urine after ingestion of blood orange juice by using nano-liquid chromatography

“…were purchased from Composite Metal Services (Hallow, Worcestershire, UK) and packed with the cyclodextrin based chiral stationary phase (CD-CSP). The CD-CSP was synthesized by grafting 2-hydroxypropyl-␤-CD onto silica gel (5 m) following an earlier described method [22,23]. Capillaries were packed in our laboratory following a previous published procedure [24].…”

“…Afterwards, a liquid-liquid extraction method was performed to recovery analytes. The stereospecific study was carried out using a phenyl-carbamate-hydroxyl-␤-cyclodextrin based stationary phase prepared using a procedure previously described [22].…”

Synthesis of novel perphenylcarbamated β‐cyclodextrin based chiral stationary phases via thiol‐ene click chemistry

“…Moreover, propranolol, alprenolol, pindolol, atropine, benzoin, and flavanone depicted higher Rs on our CD‐CSP than that of single amide linkage or multiple amide linkages based CD‐CSPs . In addition, benzoin and flavanone also showed higher Rs on our CD‐CSP than that of carbamate linkage based CD‐CSPs . Most importantly, propranolol and trans ‐stilbene, which could not be resolved on the commercially available Cyclobond I 2000 (Advanced Separation Technologies, Whippany, NJ, USA), could be readily separated on our CD‐CSP at optimized chromatographic conditions .…”

Single-walled carbon nanotube-based polymer monoliths for the enantioselective nano-liquid chromatographic separation of racemic pharmaceuticals

“…The use of buffers in mobile phase was avoided because of their negative effect on the life time of the capillary columns as well as its potential problems with nano-LC systems (e.g. precipitation into the pumps and valves) [32].…”