Enantioselective transport by a steroidal guanidinium receptor

Beatriz Baragaña, Adrian G. Blackburn, Perla Breccia, Anthony P. Davis, Javier De Mendoza, José M. Padrón-Carrillo, Pilar Prados, Jens Riedner, Johannes G. De Vries

Research output: Contribution to journalArticlepeer-review

65 Citations (Scopus)

Abstract

The cationic steroidal receptors 9 and 11 have been synthesized from cholic acid 3. Receptor 9 extracts N-acetyl-α-amino acids from aqueous media into chloroform with enantioselectivities (L:D) of 7-10:1. The lipophilic variant 11 has been employed for the enantioselective transport of N-acetylphenylalanine, a) through dichloromethane (DCM) and dichloroethane (DCE) bulk liquid membranes (U-tube apparatus), and b) through 2.5% (v/v) octanol/hexane via hollow fibre membrane contactors. Significant enantioselectivities and multiple turnovers were observed for both types of apparatus.

Original languageEnglish
Pages (from-to)2931-2936
Number of pages6
JournalChemistry - A European Journal
Volume8
Issue number13
DOIs
Publication statusPublished - 3 Jul 2002

Keywords

  • Chiral resolution
  • Enantioselectivity
  • Membranes
  • Receptors
  • Transport

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