title: Evaluation of the chiral recognition properties as well as the column performance of four chiral stationary phases based on cellulose (3,5-dimethylphenylcarbamate) by parallel HPLC and SFC.
abstract: The performance of four commercially available cellulose tris(3,5-dimethylphenylcarbamate) based chiral stationary phases (CSPs) was evaluated with parallel high performance liquid chromatography (HPLC) and super critical fluid chromatography (SFC). Retention, enantioselectivity, resolution and efficiency were compared for a set of neutral, basic and acidic compounds having different physico-chemical properties by using different mobile phase conditions. Although the chiral selector is the same in all the four CSPs, a large difference in the ability to retain and resolve enantiomers was observed under the same chromatographic conditions. We believe that this is mainly due to differences in the silica matrix and immobilization techniques used by the different vendors. An extended study of metoprolol and structure analogues gave a deeper understanding of the accessibility of the chiral discriminating interactions and its impact on the resolution of the racemic compounds on the four CSPs studied. Also, a clear difference in enantioselectivity is observed between SFC and LC mode, hydrogen bonding was found to play an important role in the differential binding of the enantiomers to the CSPs.
authors: Astra Zeneca R&D Mölndal, SE-431 83 Mölndal, Sweden. hanna.nelander@astrazeneca.com
authors: Hanna
authors: H
authors: Nelander
authors: Shalini
authors: S
authors: Andersson
authors: Kristina
authors: K
authors: Ohlén
mesh_terms: D019840:2-Propanol / Q000737:chemistry; D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D025924:Chromatography, Supercritical Fluid / Q000295:instrumentation* / Q000379:methods; D006536:Heptanes / Q000737:chemistry; D006860:Hydrogen Bonding; D008790:Metoprolol / Q000737:chemistry; D048448:Phenylcarbamates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C504080:3,5-dimethylphenylcarbamate; D006536:Heptanes; D048448:Phenylcarbamates; C065943:cellulose tris-3,5-dimethylphenyl-carbamate; D002482:Cellulose; D008790:Metoprolol; D019840:2-Propanol