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Enantioselective Transport by a Steroidal Guanidinium Receptor
Author(s) -
Baragaña Beatriz,
Blackburn Adrian G.,
Breccia Perla,
Davis Anthony P.,
de Mendoza Javier,
PadrónCarrillo José M.,
Prados Pilar,
Riedner Jens,
de Vries Johannes G.
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020703)8:13<2931::aid-chem2931>3.0.co;2-h
Subject(s) - enantioselective synthesis , dichloromethane , chemistry , cationic polymerization , cholic acid , chloroform , receptor , aqueous solution , membrane , solvent , chromatography , organic chemistry , biochemistry , bile acid , catalysis
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.