Enantiomeric resolution of chiral sulfoxides on polysaccharide phases by HPLC

Abstract

The enantiomeric resolution of chiral sulfoxides was investigated on amylose (S)‐α‐methylbenzyl carbamate phase coated on aminopropylated 7 μm silica with 500Å diameter pores. This was shown to be very successful in the separation of alkyl/aryl, aryl/aryl, and non‐aromatic sulfoxides. The effect of pore size using naked silica was also investigated, demonstrating that the pore size does not affect the resolution. © 1996 Wiley‐Liss, Inc.

A method for determination of the plasma levels of modafinil enantiomers, (±)-modafinic acid and modafinil sulphone by direct human plasma injection and bidimensional achiral–chiral chromatography

“…Derivatized polysaccharide-based stationary phases have proved to be very efficient in the resolution of a series of chiral suphoxides [12,[22][23]. The use of amylose tris[(S)-1-phenylethylcarbamate], in the reverse elution mode, showed the best performance in the separation of modafinil enantiomers, as reported before [9], and it was selected as the analytical column.…”

“…Data acquisition was done on a Shimadzu Class-VP Software. The columns were prepared as described elsewhere [11,12] and consisted of amylose tris[(S)-1-phenylethylcarbamate] coated onto APSNucleosil (7 m particle size and 500Å pore size, 20% w/w, 15 cm × 0.46 cm i.d.) as the chiral column and an octyl BSA (1.0 cm × 0.46 cm i.d., 10 m) as the restricted access media.…”

Analytical and semipreparative resolution of enatiomers of albendazole sulfoxide by HPLC on amylose tris (3,5-dimethylphenylcarbamate) chiral stationary phases

“…Amylose tris (3,5-dimethylphenylcarbamate) (ADMPC), cellulose tris (3,5-dimethylphenylcarbamate) (CDMPC), and cellulose tribenzoate (CTB) were prepared as described in Refs. [31,32]. They were coated on aminopropylated silica gel with a coating amount of 15% (w/w).…”

Enantioseparation of chiral sulfoxides and sulfinate esters by capillary electrophoresis

“…Other early work, pioneered by Farina and co-workers [8], involved the chiral separation of sulfoxides by liquid chromatography (LC) on a-lactose. Later studies progressed to using HPLC with various chiral stationary phases (CSPs) [8,9]. Welch and coworkers [10] used a p-complex normal phase chiral stationary phase, while Montanari and Cass [11] used four different CSPs (arylcarbamates of cellulose and amylose polysaccharides coated onto 3-aminopropylsilica gel) to separate a number of sulfoxides.…”

“…For sulfoxide numbers 1-6, 8, 13, 17, 19-20, 22-29, and 30-41, pure samples of the compounds were dissolved in 10 mM sodium phosphate solution at a concentration of approximately 0.1 mg/mL. Sulfoxides 7,9,11,12,and 15 were dissolved by placing roughly 0.2 mg in 3 mL of 10 mM phosphate buffer and then adding just enough methanol for total dissolution. The remaining sulfoxides (10,14,16,18,21) had severe solubility problems and in order to dissolve these samples, a saturated solution in methanol had to be prepared, and then a drop from this solution was placed in 3 mL of 10 mM sodium phosphate.…”