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Highly enantioselective separation using a supported liquid membrane encapsulating surfactant-enzyme complex.

Eijiro Miyako¹, Tatsuo Maruyama, Noriho Kamiya

¹Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, PRESTO, JST, Fukuoka 812-8581, Japan.

Journal of the American Chemical Society

|July 15, 2004

Summary

A novel supported liquid membrane (SLM) system utilizing enzyme-surfactant complexes achieved highly enantioselective separation of (S)-ibuprofen and L-phenylalanine from racemic mixtures with over 91% enantiomeric excess.

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Area of Science:

Biocatalysis
Membrane Science
Chiral Separations

Background:

Enantioselective separation is crucial for pharmaceuticals and fine chemicals.
Traditional methods for chiral resolution can be inefficient or costly.
Enzymatic catalysis offers a green and selective approach to chiral separations.

Purpose of the Study:

To develop a highly enantioselective separation system for optically active compounds.
To utilize a supported liquid membrane (SLM) with encapsulated enzyme-surfactant complexes.
To achieve efficient optical resolution of racemic ibuprofen and phenylalanine.

Main Methods:

Development of a supported liquid membrane (SLM).
Encapsulation of surfactant-enzyme complexes (lipase or alpha-chymotrypsin) within the SLM.
Employing the SLM for enantioselective transport of chiral compounds from racemic mixtures.

Main Results:

The novel SLM system demonstrated high enantioselectivity.
Achieved enantiomeric excess (ee) over 91% for both (S)-ibuprofen and L-phenylalanine.
Enzymes within the membrane phase effectively drove enantioselective transport.

Conclusions:

The developed SLM system provides an effective method for chiral resolution.
Enzyme-immobilization in SLMs is a promising strategy for enantioselective separations.
This approach offers a highly selective and efficient pathway for obtaining optically pure compounds.