Enantioresolution of Substituted 2-Methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles on Macrocyclic Antibiotic and Cyclodextrin Stationary Phases

Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase

“…This is known as the ''principle of complementary separation,'' and can be very useful when trying to optimize separations. 4,32 The ''complementary separations'' seen are unique for the oligophenolic glycopeptide antibiotics, and have not been observed for other classes of CSPs. 4 …”

Chiral separation by chromatographic and electromigration techniques. A Review

“…Hydrophobic parts of the analyte may be included into the hydrophobic basket and hydrogen bonds with the pendant arms as well as dipole stacking, ionic-, p-p interactions and steric repulsions are assumed to be the main interactions responsible for chiral recognition. Vancomycin [131] found application among others to the chiral separation of barbiturates, hydantoins, piperidine-2,6-dione and cyclic amides [136], dihydropyrimidinones [137], pyridone derivatives [138] and semi-synthetic ergot alkaloids [139]. A CSP based on vancomycin derivatized with 3,5-dimethylphenylisocyanate [131] showed different chiral recognition ability and resolved for example hydroxyzine and althiazide.…”

Evaluation of the macrocyclic antibiotic LY333328 as a chiral selector when used as a mobile phase additive in narrow bore HPLC

“…[19][20][21][22] Separation mechanisms of macrocyclic antibiotics are only partially understood at best, in part due to their large size and multiple ionization sites. Several chiral recognition forces are believed to enhance enantioseparation including ⌸-⌸ interaction, hydrogen bonding, dipole-dipole forces, steric interaction, and inclusion complexation.…”