Preparation of molecule imprinted membrane of single enantiomer of amino acid with an innovative strategy and study on its chiral recognition and resolution properties

Abstract

BACKGROUND The molecularly imprinted membranes (MIMs) with high performance are very valuable in the chiral resolution of amino acids. In this work, a novel molecularly imprinted membrane of the single enantiomer of amino acids with graft type was successfully prepared by using an advanced surface imprinting technique. The aminated microfiltration membrane of polysulfone, AMPSF membrane, was first prepared, and so a surface‐initiating system of ‐NH2/S2O8‐ was constituted. In an aqueous solution, the molecules of dimethylaminoethyl methacrylate (DMAEMA) as functional monomer were combined around L‐glutamic acid (L‐Glu) as template by right of electrostatic interaction and hydrogen bonding. By initiating of ‐NH2/S2O8‐ system, DMAEMA and the crosslinking agent N,N′‐Methylenebisacrylamide (MBA) produced graft/crosslinking‐polymerization on the surface of AMPSF membrane, whereas L‐Glue molecules were wrapped within the grafted polymer layer, obtaining grafting type L‐Glue molecule‐imprinted membrane (L‐Glue‐MIM). The ability of the chiral recognition and enantioseparation of L‐Glue‐MIM were examined. RESULTS The experimental results show that L‐Glue‐MIM possesses specific chiral recognition selectivity and excellent enantioseparation ability. In the permeation experiment, L‐Glue molecules in the raceme solution can smoothly pass across L‐Glue‐MIM, but D‐Glue molecules are seriously blocked. As a result, Glu raceme solution is well separated, and the optical purity (ee value) of the penetrating fluid gets up to 82%. CONCLUSION Grafting type molecularly imprinted membrane of the single enantiomer of amino acids was successfully prepared by using an innovative and advanced surface‐imprinting technique of “synchronously graft‐polymerizing and molecule imprinting”, and it supplies a newer route to prepare imprinted membrane with high performance for chiral resolution of amino acids and other chiral drugs. Such study is reported for the first time. © 2017 Society of Chemical Industry

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

“…Hence, the penetrating fluid achieved an enantiomeric excess higher than 82%. Moreover, comparing with the previous method that they used to prepare imprinted membranes, i.e., "pre-graft polymerization and post-imprinting" [150], it was concluded that the present method was more effective and simple, and the obtained membranes revealed a better performance [151].…”

“…The same group successfully prepared a novel grafting-type MIM of a single enantiomer of amino acids by an innovative and advanced surface-imprinting technique of "synchronously graft-polymerizing and molecule imprinting" [151]. Firstly, the aminated microfiltration membrane of polysulfone, AMPSF membrane, was prepared creating a surface-initiating system of -NH 2 /S 2 O 8 .…”

Preparation of PSSS‐grafted polysulfone microfiltration membrane and its rejection and removal properties towards heavy metal ions

“…In the spectrum of CMPSF membrane, there are two characteristic absorption bands of chloromethyl groups at 1441 and 660 cm −1 , and they are attributed to the in‐plane bending vibration absorption of C─H bond and the stretching vibration of C─Cl bond in the group ─CH 2 Cl, respectively. By contrast, in the spectrum of PSF‐DEA membrane, the two characteristic absorption bands of chloromethyl groups have weakened greatly.…”

“…In order to develop grafting‐type functional composite membranes, it is a promising method to constitute surface‐initiating systems at the interface between the substrate membranes and the solutions containing functional monomers, and the graft polymerization of the functional monomers can be conducted under mild conditions, resulting in the functional composite membranes with high performance. Previously, we designed and constituted a surface‐initiating system of primary amine group/persulfate (─NH 2 /S 2 O 8 2− ) at the interface between chloromethylated polysulfone (CMPSF) microfiltration membranes and aqueous solution, and the graft polymerizations of methacrylic acid (MAA) and dimethylaminoethyl methacrylate (DMAEMA) were successfully realized on the surface of CMPSF membrane as substrate membrane . The obtained grafting‐type composite membranes were used for the separations of alkaloids and acidic amino acids.…”

Microfiltration membrane possessing chelation function and its adsorption and rejection properties towards heavy metal ions

“…Chloromethylated polysulfone (CMPSF) was self‐synthesized and its chlorine content or the content of chloromethyl group was 2 mmol g −1 . Then CMPSF microfiltration membrane with a thickness of 200 µm and with a bore diameter range of 0.1‐1 µm was prepared by the method of immersion‐precipitation phase transformation . 3‐Hydroxy‐N,N‐diethylaniline (HDEA) was Aladdin's reagent, and purchased from Shanghai Aladdin Bio‐Chem Technology Co., Ltd (Shanghai, China).…”