Enantioselective transport by a steroidal guanidinium receptor.
The cationic steroidal receptors 9 and 11 have been synthesized from cholic acid 3. Receptor 9 extracts N-acetyl-alpha-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.
Baragaña
Beatriz
B
Department of Chemistry, Trinity College Dublin 2 Ireland.
Blackburn
Adrian G
AG
Breccia
Perla
P
Davis
Anthony P
AP
de Mendoza
Javier
J
Padrón-Carrillo
José M
JM
Prados
Pilar
P
Riedner
Jens
J
de Vries
Johannes G
JG
D002352:Carrier Proteins / Q000138:chemical synthesis; D019791:Guanidine / Q000737:chemistry*; D008567:Membranes, Artificial; D008752:Methylene Chloride; D008958:Models, Molecular; D018716:Molecular Mimicry; D011987:Receptors, Steroid / Q000737:chemistry*; D013237:Stereoisomerism
D002352:Carrier Proteins; D008567:Membranes, Artificial; D011987:Receptors, Steroid; D008752:Methylene Chloride; D019791:Guanidine