Polymeric Membranes for Chiral Separation of Pharmaceuticals and Chemicals

Higuchi, Akon; Tamai, Miho; Ko, Yi An; Tagawa, Yoh‐ichi; Wu, Yuan Hsuan; Freeman, Benny D.; Bing, Jun Tang; Chang, Yung; Ling, Qing

doi:10.1080/15583721003698853

Cited by 138 publications

(87 citation statements)

References 82 publications

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“…The permselectivities for the present molecularly imprinted nanofiber membranes were not so high comparing with membranes previously reported [39][40][41]. The permselectivity is thought to be greatly dependent on adsorption selectivity.…”

Section: Chiral Separationmentioning

confidence: 50%

Chiral separation with molecularly imprinted polysulfone-aldehyde derivatized nanofiber membranes☆

Sueyoshi

Utsunomiya

Yoshikawa

et al. 2012

Journal of Membrane Science

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a b s t r a c tMolecularly imprinted membranes (MIPMs) and molecularly imprinted nanofiber membranes (MINFMs) were prepared from polysulfone with aldehyde (PSf-CHO-05 or PSf-CHO-10) and N-␣-benzyloxycarbonyl-d-glutamic acid (Z-d-Glu) or N-␣-benzyloxycarbonyl-l-glutamic acid (Z-l-Glu) as a print molecule. Those two types of molecularly imprinted membrane, such as MIPMs and MINFMs, incorporated the enantiomer, of which absolute configuration was same as that of the print molecule, in preference to the corresponding antipode. In other words, the membranes imprinted by the d-isomer preferentially adsorbed the d-isomer and vice versa. Those two types of membrane showed chiral separation ability by membrane transport. Against expectation, transport of the enantiomer preferentially adsorbed in the membrane was retarded, in other words, the enantiomer less adsorbed in the membrane was selectively transported. The fluxes through the molecularly imprinted nanofiber membranes gave one to two orders of magnitude higher than those of usual molecularly imprinted membranes without depression of permselectivity. The present study demonstrated that molecularly imprinted nanofiber membrane gave high flux without depression of permselectivity. A breakthrough in membrane separation would be realized by adopting molecularly imprinted nanofiber membranes.

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Section: Chiral Separationmentioning

confidence: 50%

Chiral separation with molecularly imprinted polysulfone-aldehyde derivatized nanofiber membranes☆

Sueyoshi

Utsunomiya

Yoshikawa

et al. 2012

Journal of Membrane Science

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“…From this, the study on membrane materials for chiral separation is interesting and vital. [9][10][11][12] When the optical resolution is carried out by applying membrane technology, it is required that there should be, at least, one chiral environment in the given membrane separation system; for instance, (i) optical resolution with liquid membranes containing transporters bearing chiral recognition sites, [13][14][15][16] (ii) chiral separation with membranes prepared from polymeric materials having chiral 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.…”

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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“…149 Adsorption-type enantioselective membranes and membrane-assisted resolution systems with non-enantioselective solid membranes have attracted much attention recently. [150][151][152][153] If the enantioselective membrane is possible to recycle, the enantiomer membrane extraction technology will afford an efficient, practical way for the chiral resolution. As a result of the separation process, diastereomeric mixtures can be resolved, and enantioselectivities up to 95% ee for some racemates can be then achieved.…”

Section: Enantioselective Extractions Enantioselective Liquid-liquid mentioning

confidence: 99%

Principles, Concepts and Strategies of Stereoselective Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

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Polymeric Membranes for Chiral Separation of Pharmaceuticals and Chemicals

Cited by 138 publications

References 82 publications

Chiral separation with molecularly imprinted polysulfone-aldehyde derivatized nanofiber membranes☆

Chiral separation with molecularly imprinted polysulfone-aldehyde derivatized nanofiber membranes☆

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

Principles, Concepts and Strategies of Stereoselective Synthesis

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