Nilusha L Padivitage1, Jonathan P Smuts1, Zachary S Breitbach2, Daniel W Armstrong2, Alain Berthod3. 1. Department of Chemistry, University of Texas at Arlington, Planetarium Place, Arlington, TX 76019, USA. 2. Department of Chemistry, University of Texas at Arlington, Planetarium Place, Arlington, TX 76019, USA ; AZYP LLC, 700 Planetarium Place, Arlington, TX 76019, USA. 3. Institut des Sciences Analytiques, Université de Lyon 1, CNRS, 5 rue de la Doua, 69100 Villeurbanne, France.
Abstract
The cyclofructan 6 (CF6) macrocyclic-oligosaccharide was derivatized with five different substituents able to bear positive charges: propyl imidazole (IM) methyl benzimidazole (BIM), dimethyl aminopropyl (AP), pyridine (PY) and dimethyl aminophenyl (DMAP). The derivatized cyclofructans were reacted with triethoxysilyl-propylisocyanate as a linker to bond them to 5 μm spherical silica gel particles and then used to prepare HPLC columns. The bonded silica particles were analyzed to establish the bonding densities. A set of 34 chiral compounds including acids, neutral compounds and bases was tested with nine different mobile phase compositions including two reverse phase (RP) acetonitrile/pH 4 buffer, three polar organic (PO) acetonitrile/methanol and four normal phase (NP) heptane/ethanol mobile phases. No compounds could be separated in the RP mode. Eight compounds only could be enantioseparated in the PO mode and 21 compounds in the NP mode. The most effective chiral stationary phase was the propyl imidazole derivatized CF6 phase, provided that no more than six imidazole substituents and two linkers are attached per CF6 unit.
The cyclofructan 6 (CF6) macrocyclic-oligosaccharide was derivatized with five different substituents able to bear n class="Chemical">positive charges: propyl imidazole (IM) methyl benzimidazole (BIM), dimethyl aminopropyl (AP), pyridine (PY) and dimethyl aminophenyl (DMAP). The derivatized cyclofructans were reacted with triethoxysilyl-propylisocyanate as a linker to bond them to 5 μm spherical silica gel particles and then used to prepare HPLC columns. The bonded silica particles were analyzed to establish the bonding densities. A set of 34 chiral compounds including acids, neutral compounds and bases was tested with nine different mobile phase compositions including two reverse phase (RP) acetonitrile/pH 4 buffer, three polar organic (PO) acetonitrile/methanol and four normal phase (NP) heptane/ethanol mobile phases. No compounds could be separated in the RP mode. Eight compounds only could be enantioseparated in the PO mode and 21 compounds in the NP mode. The most effective chiral stationary phase was the propyl imidazole derivatized CF6 phase, provided that no more than six imidazole substituents and two linkers are attached per CF6 unit.
Authors: Yi Jun Zhang; Ming Xian Huang; Yu Ping Zhang; Daniel Wayne Armstrong; Zachary S Breitbach; Jae Jeong Ryoo Journal: Chirality Date: 2013-08-13 Impact factor: 2.437
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