title: Enantioseparation of α-Hydroxyallylphosphonates and Phosphonoallylic Carbonate Derivatives on Chiral Stationary Phases Using Sequential UV, Polarimetric, and Refractive Index Detection.
abstract: Chromatographic separation of the enantiomers of parent compounds dimethyl α-hydroxyallyl phosphonate and 1-(dimethoxyphosphoryl) allyl methyl carbonate was demonstrated by high-performance liquid chromatography (HPLC) using Chiralpak AS-H and ad-H chiral stationary phases (CSP), respectively, using a combination of UV, polarimetric, and refractive index detectors. A comparison was made of the separation efficiency and elution order of enantiomeric α-hydroxyallyl phosphonates and their carbonate derivatives on commercially available polysaccharide AS, ad, OD, IC-3, and Whelk-O 1 CSPs. In general, the α-hydroxyallyl phosphonates were resolved on the AS-H CSP, whereas the carbonate derivatives and were preferentially resolved on the ad-H CSP. The impact of aryl substitution on the resolution of analytes and was evaluated. Thermodynamic parameters determined for enantioselective adsorption hydroxyphosphonates and on the AS-H CSP and carbonate on the ad-H CSP demonstrated enthalpic control for separation of the enantiomers. Chirality 28:656-662, 2016. © 2016 Wiley Periodicals, Inc.
authors: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri, USA.
authors: Bruce C
authors: BC
authors: Hamper
authors: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri, USA.
authors: Michael P
authors: MP
authors: Mannino
authors: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri, USA.
authors: Melissa E
authors: ME
authors: Mueller
authors: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri, USA.
authors: Liam T
authors: LT
authors: Harrison
authors: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri, USA.
authors: Christopher D
authors: CD
authors: Spilling
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry / Q000302:isolation & purification*; D000688:Amylose / Q000031:analogs & derivatives; D002219:Carbamates; D002254:Carbonates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000302:isolation & purification*; D011134:Polysaccharides / Q000737:chemistry; D012031:Refractometry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
chemical_list: C000625946:1-(dimethoxyphosphoryl)allyl methyl carbonate; D000498:Allyl Compounds; D002219:Carbamates; D002254:Carbonates; D009943:Organophosphorus Compounds; D011134:Polysaccharides; C445088:chiralpak AS; C000625947:dimethyl alpha-hydroxyallyl phosphonate; D000688:Amylose
keywords: HPLC; chiral stationary phases; enantiomer separation; multiple detectors; phosphonoallylic carbonates; polarimetric detection; α-hydroxy phosphonates