Enantioselective molecularly imprinted polymer membranes

Dzgoev, Anatoli; Haupt, Karsten

doi:10.1002/(sici)1520-636x(1999)11:5/6<465::aid-chir18>3.0.co;2-v

Cited by 77 publications

(46 citation statements)

References 13 publications

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“…Specialty membranes can be prepared by applying molecular imprinting. [4][5][6][7] Various polymeric materials, which can construct and maintain their structure, such as synthetic polymers, [8][9][10][11][12] derivative of natural polymers, [13] oligopeptide derivatives, [14] and natural polymers, [15] were converted into molecular recognition materials or membranes by applying an alternative molecular imprinting. [16,17] In earlier work, we studied the chiral molecular recognition properties of molecularly imprinted dense membranes prepared from non-chiral carboxylated polysulfone (PSf).…”

Section: Introductionmentioning

confidence: 99%

Molecularly Imprinted Nanofiber Membranes from Carboxylated Polysulfone by Electrospray Deposition

Yoshikawa

Nakai

Matsumoto

et al. 2007

Macromol. Rapid Commun.

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It is demonstrated that polymeric materials can be directly converted into molecular (chiral) recognition nanofiber membranes by simultaneously applying an electrospray deposition and an alternative molecular imprinting during the membrane preparation process. Polysulfone with a degree of substitution of 0.88 was adopted as the candidate polymeric material for molecularly imprinted nanofiber membranes. Molecularly imprinted nanofiber membranes imprinted by Z‐D‐Glu recognize the D‐isomer in preference to the corresponding L‐isomer and vice versa. The amino acid preferentially incorporated into the membrane is selectively permeated through the membrane by using a concentration gradient as a driving force for membrane transport.magnified image

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Section: Introductionmentioning

confidence: 99%

Molecularly Imprinted Nanofiber Membranes from Carboxylated Polysulfone by Electrospray Deposition

Yoshikawa

Nakai

Matsumoto

et al. 2007

Macromol. Rapid Commun.

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“…Two types of membrane processes for enantiomer separations are often employed: 1) separations with enantioselective membranes, and 2) separations with nonchiral membranes. Examples of the first type are membranes containing proteins, 4,5 chiral polymers, 6,7 molecularly imprinted membranes, [8][9][10] or emulsion liquid membranes. [11][12][13] In the second type of membrane processes, the membranes are used to retain one phase or two (im)miscible phases of which at least one is enantioselective.…”

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confidence: 99%

Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

et al. 2000

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A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the alpha-amino acids phenylalanine, phenylglycine, O-methyltyrosine, isoleucine, and leucine good separation was obtained using cholesteryl L-glutamate and Cu(II) ions as chiral selector with an operational enantioselectivity (alpha(op)) up to 14.5 for phenylglycine. From a wide set of substrates, including four beta-amino acids, it was concluded that the performance of this system is determined by two factors: the hydrophobicity of the racemic amino acid, which results in a partitioning of the racemic amino acid over micelle and aqueous solution, and the stability of the diastereomeric complex formed upon binding of the amino acid with the chiral selector. The chiral hydrophobic cholesteryl anchor of the chiral selector also plays an active role in the recognition process, since inversion of the chirality of the glutamate does not yield the reciprocal enantioselectivities. However, if the cholesteryl group is replaced by a nonchiral alkyl chain, reciprocal operational enantioselectivities are found with enantiomeric glutamate selectors.

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“…Such transport phenomena have often been observed in chiral separation [19,22,29,30,35]. Retarded transport of enantiomer preferentially incorporated into the membrane might be due to the relatively strong interaction between the enantiomer and the membrane.…”

Section: Versamentioning

confidence: 91%

“…Membrane-based chiral separation has been studied in the form of liquid [12][13][14] and polymeric membranes [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] with chiral selector or chiral environment. The authors' research group studied chiral separation with molecularly imprinted membranes [17,20,22,30] and membranes [28][29][30][31] bearing amino acid residues.…”

Section: Introductionmentioning

confidence: 99%

Electrospun nanofiber membranes from polysulfones with chiral selector aimed for optical resolution

Mizushima

Yoshikawa

et al. 2012

European Polymer Journal

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/npsi/ctrl?action=rtdoc&an=20637155&lang=en http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=20637155&lang=fr READ THESE TERMS AND CONDITIONS CAREFULLY BEFORE USING THIS WEBSITE.http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=en Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, consultez la première page de la revue dans laquelle son article a été publié afin de trouver ses coordonnées. Si vous n'arrivez pas à les repérer, communiquez avec nous à PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca. Questions?Contact the NRC Publications Archive team at PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca. If you wish to email the authors directly, please see the first page of the publication for their contact information. NRC Publications Archive Archives des publications du CNRCThis publication could be one of several versions: author's original, accepted manuscript or the publisher's version. / La version de cette publication peut être l'une des suivantes : la version prépublication de l'auteur, la version acceptée du manuscrit ou la version de l'éditeur. For the publisher's version, please access the DOI link below./ Pour consulter la version de l'éditeur, utilisez le lien DOI ci-dessous.http://doi.org/10.1016/j.eurpolymj.2012.07.003European Polymer Journal, 48, 10, pp. 1717Journal, 48, 10, pp. -1725Journal, 48, 10, pp. , 2012 ABSTRACTPolysulfones with three types of alanyl residues, such as N-!-acetylalanine (Ac-Ala-OH), N-!-benzoylalanine (Bzo-Ala-OH), and N-!-benzyloxycarbonylalanine (Z-Ala-OH), as chiral selectors were prepared by polymer reaction. The resulting modified polysulfones showed chiroptical properties, indicating that the chiral selector residues were successfully introduced into the polysulfone. Nanofiber membranes prepared from the polymeric materials showed adsorption selectivity toward mixtures of racemic Glu, which were adopted as model racemates. Flux values for the nanofiber membranes were enhanced two to three orders of magnitude in comparison with the corresponding typical membranes, but without reduction in permselectivity. In the present study, it is shown that nanofiber is a suitable membrane form not only for molecularly imprinted membranes, but it exhibits enhanced throughput in comparison with typical dense membranes without concurrent reduction in permselectivity.

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Enantioselective molecularly imprinted polymer membranes

Cited by 77 publications

References 13 publications

Molecularly Imprinted Nanofiber Membranes from Carboxylated Polysulfone by Electrospray Deposition

Molecularly Imprinted Nanofiber Membranes from Carboxylated Polysulfone by Electrospray Deposition

Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

Electrospun nanofiber membranes from polysulfones with chiral selector aimed for optical resolution

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