Membranes based on poly(γ-methyl-l-glutamate): synthesis, characterization and use in chiral separations

Thoelen, Carla; bruyn, Mario De; Theunissen, Elisabeth; Kondo, Yoshiko; Vankelecom, Ivo F.J.; Grobet, Piet J.; Yoshikawa, Masakazu; Jacobs, Pierre

doi:10.1016/s0376-7388(00)00687-6

Cited by 52 publications

(25 citation statements)

References 18 publications

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“…Those molecularly imprinted membranes show chiral separation abilities when a concentration gradient or an applied potential difference is applied as a driving force for membrane transport. environment in their main chains or in their side ones, [17][18][19][20][21][22][23][24][25][26][27][28] (iii) optical resolution with membrane with chiral helicity, [29] (iv) that with achiral membrane and affinity macroligand, such as bovine serum albumin (BSA), [30,31] by applying sieving effect, and (v) kinetic resolution with enzyme. [32,33] The authors' research group focused their attentions on chiral separation with molecularly imprinted membranes, [22,24] molecularly imprinted nanofiber membranes, [34,35]] membranes with chiral environment, [26] and membranes from chiral polyamides consisting of amino acid residues.…”

Section: Introductionmentioning

confidence: 99%

Polyurea With L‐Lysinyl Residues as Components: Application to Membrane Separation of Enantiomers

Hatanaka

Nishioka

Yoshikawa

2011

Macro Chemistry & Physics

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Novel polyureas are synthesized from lysinyl residues. The polyurea thus prepared yields a durable self‐standing membrane that can be converted into a molecular recognition material by using Z‐D‐Glu or Z‐L‐Glu as a print molecule. The Z‐D‐Glu molecularly imprinted membrane adsorbes the D‐isomer of Glu in preference to the corresponding L‐Glu and vice versa. Even though the polyurea consists of L‐lysinyl residues, both Z‐D‐Glu and Z‐L‐Glu work as print molecules to construct molecular (chiral) recognition sites in the membrane. Those molecularly imprinted membranes show chiral separation abilities when a concentration gradient or an applied potential difference is applied as a driving force for membrane transport. magnified image

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Section: Introductionmentioning

confidence: 99%

Polyurea With L‐Lysinyl Residues as Components: Application to Membrane Separation of Enantiomers

Hatanaka

Nishioka

Yoshikawa

2011

Macro Chemistry & Physics

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“…Such separation is known as carrier facilitated transport. Carrier-facilitated transport of chiral compounds has been studied extensively using different types of chiral carriers [79][80][81]. The liquid membranes containing various kinds of chiral selector and enantiomers recognizing carriers such as chiral crown ethers [82], cyclodextrins [83][84][85][86][87], polysaccharides [88], biomacromolecules, [89] and calixarenes [90], were studied.…”

Section: Optical Resolution Through Liquid Membranesmentioning

confidence: 99%

“…The selectivity of membrane for isomers of tryptophan and tyrosin was demonstrated. Considerable efforts have been made in recent years to develop chiral selective membranes and membranebased process for optical resolution separation [79,94]. In this approach polymer membranes having inbuilt capability to separate enantiomers were prepared and experimented.…”

Section: Optical Resolution Through Chiral Membranesmentioning

confidence: 99%

Methods for separation of organic and pharmaceutical compounds by different polymer materials

Ingole

2014

Korean J. Chem. Eng.

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The discrimination of enantiomers is a challenging task in separation technology, and using a membrane is most promising for separating enantiomers from racemic mixture. The optical resolution of chiral compounds is of interest to researchers working in a variety of fields from analytical, organic and medicinal chemistry, to pharmaceutics and materials, to process engineering for fabricating pharmaceuticals, agrochemicals, fragrances and foods, and so on. There is considerable demand for separation techniques appropriate for the large-scale resolution of chiral molecules. The separation of chiral compounds using chiral or achiral/non-chiral polymeric membranes with or without chiral selector represents a promising system for future commercial applications. This review focuses on an active field of chiral separation, membrane-based enantioseparation technique, which has potential for large-scale production of singleenantiomers. Enantiomeric separation by membrane processes has been studied using various configurations of liquid and solid polymer membranes. Selectivity and permeability of liquid-membranes is reasonably good because the rate of diffusion of solute molecules is high in liquids but has inferior durability and stability. Solid polymer membranes have inferior permeability because diffusion of solute through solids is slow but quite stable and durable; however, commercial application of membrane technology for optical resolution is yet to be realized. Several chiral separation membranes were prepared from chiral polymers where enantioselectivity was generated from chiral carbons in the main chain. However, it is rather tricky to generate excellent chiral separation membranes from chiral polymers alone, because racemic penetrants mainly encounter the flexible side chains of the membrane polymers.

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“…Several membranes were prepared from chiral polymers where enantioselectivity was generated from chiral carbons in the main chain. Poly(γ-methyl-L-glutamate) [77,78], alginate [79,80], chitosan [79,81], cellulose [81][82][83] and their derivatives are frequently used as chiral polymers for the preparation of chiral membranes. However, sometimes it is rather difficult to make high efficient chiral separation with membranes from chiral polymers alone, when the enantiomers interact with the flexible side chains of the membrane polymers not comprising chiral sites important for the effectiveness of the molecular interactions and, consequently, enantiorecognition.…”

Section: Introductionmentioning

confidence: 99%

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

2017

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Given the importance of chirality in the biological response, regulators, industries and researchers require chiral compounds in their enantiomeric pure form. Therefore, the approach to separate enantiomers in preparative scale needs to be fast, easy to operate, low cost and allow obtaining the enantiomers at high level of optical purity. A variety of methodologies to separate enantiomers in preparative scale is described, but most of them are expensive or with restricted applicability. However, the use of membranes have been pointed out as a promising methodology for scale-up enantiomeric separation due to the low energy consumption, continuous operability, variety of materials and supports, simplicity, eco-friendly and the possibility to be integrated into other separation processes. Different types of membranes (solid and liquid) have been developed and may provide applicability in multi-milligram and industrial scales. In this brief overview, the different types and chemical nature of membranes are described, showing their advantages and drawbacks. Recent applications of enantiomeric separations of pharmaceuticals, amines and amino acids were reported.

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Membranes based on poly(γ-methyl-l-glutamate): synthesis, characterization and use in chiral separations

Cited by 52 publications

References 18 publications

Polyurea With L‐Lysinyl Residues as Components: Application to Membrane Separation of Enantiomers

Polyurea With L‐Lysinyl Residues as Components: Application to Membrane Separation of Enantiomers

Methods for separation of organic and pharmaceutical compounds by different polymer materials

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

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