Chiral discrimination of complexes between benzyloxycarbonylglycyl-l-proline and 4-hydroxy-2-dipropylaminoindan in ion-pair chromatography: A molecular mechanics study
作者： Kristina Luthman , Anders Vang Jensen , Uli Hacksell , Anders Karlsson , Curt Pettersson
DOI: 10.1016/0021-9673(94)80414-1
关键词: Enantiomer 、 Chemistry 、 Bicyclic molecule 、 Diastereomer 、 Chromatography 、 Adduct 、 Tetralin 、 Ionic bonding 、 Hydrogen bond 、 Intramolecular force
摘要: Abstract The separation of the enantiomers 4-hydroxy-2-dipropylaminoindan (USDA-46) was accomplished by ion-pair chromatography using benzyloxycarbonylglycyl- l -proline ( -ZGP) as a chiral selector in mobile phase. Molecular mechanics calculations (MMX) were performed to model formation diastereomeric complexes -ZGP and USDA-46. Complexes generated manual dockings variety different conformations each component an automated Monte Carlo search MacroModel. found be stabilized reinforced ionic interaction, inter- intramolecular hydrogen bonds attractive aromatic interactions. Geometries energies complex calculated determine dynamic measures total partial surface areas dipole moments. results combined with data from study on series phenolic aminotetralin derivatives. previously established correlation between coefficient α tetralin derivatives difference unsaturated area corroborated obtained
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