Enantiomeric resolution of supramolecular helicates with different surface topographies

作者: Jessica M. C. A. Kerckhoffs , Jemma C. Peberdy , Isabelle Meistermann , Laura J. Childs , Christian J. Isaac

DOI: 10.1039/B614093A

关键词:

摘要: The enantiomeric resolution of an extended range di-metallo supramolecular triple-helical molecules are reported. ligands for all complexes symmetric with two units containing aryl group linked via imine bond to a pyridine. Alkyl substituents have been attached in different positions on the ligand backbone. Previous work parent compound, whose molecular formula is [Fe2(C25H20N4)3]Cl4, showed that it could be resolved into enantiomerically pure solutions using cellulose and 20 mM aqueous sodium chloride. In this mobile phases investigated see if separation speed elution increased amount NaCl co-eluted compounds decreased. Methanol, ethanol acetonitrile were considered, together : organic mixtures. Effective was most often achieved when 90% 10% (aq) w/v, which gives scope scaling up incorporate use HPLC. overall efficient (i.e. fastest) generally where column packed first eluted 100% acetonitrile, then 75% 25% until M enantiomer had fully finally P collected. sequence eluents ensured minimum accompanying enantiomers total solvent being required elute enantiomers, especially second one, from column. No helicate methyl groups pyridine rings also adverse effect resolution.

参考文章(32)
Jean‐Marie Lehn, Supramolecular Chemistry: Concepts and Perspectives Malta II : Frontiers of Chemical Sciences 2 : Research and Education in the Middle East, Malta. ,(1995) , 10.1002/3527607439
Alison Rodger, Bengt Nordén, P. Mark Rodger, Paula J. Bates, DNA as a Catalyst and Catalytic Template for the Racemisation of Metal Tris-Phenanthroline Complexes European Journal of Inorganic Chemistry. ,vol. 2002, pp. 49- 53 ,(2002) , 10.1002/1099-0682(20021)2002:1<49::AID-EJIC49>3.0.CO;2-8
J.Mark Green, Rosemarie Jones, Richard D. Harrison, D.Scott Edwards, Joseph L. Glajch, Liquid chromatographic separation of radiopharmaceutical ligand enantiomers Journal of Chromatography A. ,vol. 635, pp. 203- 209 ,(1993) , 10.1016/0021-9673(93)80362-C
Todd J. Rutherford, Paul A. Pellegrini, Janice Aldrich-Wright, Peter C. Junk, F. Richard Keene, Isolation of Enantiomers of a Range of Tris(bidentate)ruthenium(II) Species Using Chromatographic Resolution and Stereoretentive Synthetic Methods European Journal of Inorganic Chemistry. ,vol. 1998, pp. 1677- 1688 ,(1998) , 10.1002/(SICI)1099-0682(199811)1998:11<1677::AID-EJIC1677>3.0.CO;2-S
Alison Rodger, Karen J. Sanders, Michael J. Hannon, Isabelle Meistermann, Andrew Parkinson, Daniel S. Vidler, Ian S. Haworth, DNA structure control by polycationic species: polyamine, cobalt ammines, and di-metallo transition metal chelates Chirality. ,vol. 12, pp. 221- 236 ,(2000) , 10.1002/(SICI)1520-636X(2000)12:4<221::AID-CHIR9>3.0.CO;2-3
Kazuaki Yamanari, Motonori Nakamichi, Optical resolution of anionic complexes by a chromatographic column containing (β-cyclodextrinato)bis(ethylenediamine)cobalt(III)(1+) chloride Journal of The Chemical Society, Chemical Communications. pp. 1723- 1724 ,(1989) , 10.1039/C39890001723
Claude Piguet, Gérald Bernardinelli, Gérard Hopfgartner, Helicates as Versatile Supramolecular Complexes. Chemical Reviews. ,vol. 97, pp. 2005- 2062 ,(1997) , 10.1021/CR960053S
Daniel W. Armstrong, Wade. Demond, Bronislaw P. Czech, Separation of metallocene enantiomers by liquid chromatography: chiral recognition via cyclodextrin bonded phases Analytical Chemistry. ,vol. 57, pp. 481- 484 ,(1985) , 10.1021/AC50001A037
Michael J. Hannon, Laura J. Childs, Helices and Helicates: Beautiful Supramolecular Motifs with Emerging Applications Supramolecular Chemistry. ,vol. 16, pp. 7- 22 ,(2004) , 10.1080/10610270310001632386