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

doi:10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO;2-H

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

Biological Chemistry and Drug Discovery

Research output: Contribution to journal › Article › peer-review

67 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 language	English
Pages (from-to)	2931-2936
Number of pages	6
Journal	Chemistry - A European Journal
Volume	8
Issue number	13
DOIs	https://doi.org/10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO;2-H
Publication status	Published - 3 Jul 2002

Keywords

Chiral resolution
Enantioselectivity
Membranes
Receptors
Transport

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO;2-H

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title = "Enantioselective transport by a steroidal guanidinium receptor",

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.",

keywords = "Chiral resolution, Enantioselectivity, Membranes, Receptors, Transport",

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AU - Baragaña, Beatriz

AU - Blackburn, Adrian G.

AU - Breccia, Perla

AU - Davis, Anthony P.

AU - De Mendoza, Javier

AU - Padrón-Carrillo, José M.

AU - Prados, Pilar

AU - Riedner, Jens

AU - De Vries, Johannes G.

PY - 2002/7/3

Y1 - 2002/7/3

N2 - 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.

AB - 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.

KW - Chiral resolution

KW - Enantioselectivity

KW - Membranes

KW - Receptors

KW - Transport

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JO - Chemistry - A European Journal

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ER -

Enantioselective transport by a steroidal guanidinium receptor

Abstract

Keywords

ASJC Scopus subject areas

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