Molecularly imprinted polymeric membranes for optical resolution

Yoshikawa, Masakazu; Izumi, Jun; Kitao, Toshio; Koya, Susumu; Sakamoto, Shunji

doi:10.1016/0376-7388(95)00160-8

Cited by 107 publications

(55 citation statements)

References 17 publications

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“…From the results summarized in Table 1 and those reported previously (1)(2)(3)(4)(5), it can be said that the chiral recognition site was induced by the presence of print molecule Z-D-Glu or Z-L-Glu in the membrane preparation process. A representative scheme for the formation of molecularly imprinted polymeric membranes and the recognition of racemic amino acid mixtures are given in Figure 1.…”

Section: Resultssupporting

confidence: 61%

“…We have reported that optical resolution of racemic α-amino acids was attained by molecularly imprinted polymeric membranes, which were prepared from polystyrene resins bearing oligopeptide (1)(2)(3)(4) or derivatives of natural polymer (5). The molecular imprinting technique, first proposed by Wulff (6), is a facile one for introducing molecular recognition sites into polymeric materials (7)(8)(9).…”

Section: Introductionmentioning

confidence: 99%

“…We have applied an alternative molecular imprinting technique to our studies (1)(2)(3)(4)(5) that is based on inducing "molecular memory" in a membrane substrate at the same time of gelation. An optically active imprint molecule is combined with the membrane polymer containing a functional group moiety in solution.…”

Section: Introductionmentioning

confidence: 99%

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Carboxylated polysulfone membranes having a chiral recognition site induced by an alternative molecular imprinting technique

et al. 1998

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Carboxylated polysulfone membranes having a chiral recognition site induced by an alternative molecular imprinting technique Yoshikawa, M.; Izumi, J-I; Ooi, T.; Guiver, Michael; Robertson, Gilles Polymer Bulletin 40, 517-524 (1998) SUMMARYMolecularly imprinted polymeric membranes were prepared from carboxylated polysulfone. Membranes imprinted by Z-D-Glu recognize the D-isomer in preference to the corresponding L-isomer, and vice versa. The amino acid preferentially adsorbed by the membrane was also selectively permeated by electrodialysis. INTRODUCTIONWe have reported that optical resolution of racemic α-amino acids was attained by molecularly imprinted polymeric membranes, which were prepared from polystyrene resins bearing oligopeptide (1-4) or derivatives of natural polymer (5). The molecular imprinting technique, first proposed by Wulff (6), is a facile one for introducing molecular recognition sites into polymeric materials (7-9).We have applied an alternative molecular imprinting technique to our studies (1-5) that is based on inducing "molecular memory" in a membrane substrate at the same time of gelation. An optically active imprint molecule is combined with the membrane polymer containing a functional group moiety in solution. The membrane polymer assumes a favourable conformation for the functional group to interact with the imprint molecule. Upon gelation and membrane formation, a "molecular memory" of the optical isomer is retained by the formed membrane, such that it recognizes or favours interaction with isomers of the same configuration. The present work concerns the formation of molecularly imprinted polymeric membranes obtained from an entirely non-chiral synthetic polymer having carboxyl groups. The chiral recognition ability of these imprinted polymeric membranes derived from carboxylated polysulfone was investigated.

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Section: Resultssupporting

confidence: 61%

Section: Introductionmentioning

confidence: 99%

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Carboxylated polysulfone membranes having a chiral recognition site induced by an alternative molecular imprinting technique

et al. 1998

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“…Against this, molecular imprinting technique [4][5][6][7] would introduce molecular recognition sites into polymeric membranes without such an effort mentioned above and is perceived to be one of the most facile ways to give polymeric membranes substrate specificity [8][9][10][11]. Among molecular imprinting techniques, an alternative molecular imprinting is a facile way to introduce molecular recognition sites into polymeric membranes.…”

Section: Introductionmentioning

confidence: 99%

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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“…It is, however, difficult to apply conventional molecular imprinting techniques to the present study. This led us to develop an alternative molecular imprinting technique (10)(11)(12)(13)(14); that is, the "molecular memory" of the substrate to be recogniz ed is induced in the membrane at the same time that the polymeric construction is prepared from the polymer solution.…”

Section: Introductionmentioning

confidence: 99%

Chiral Recognition of N-.ALPHA.-Acetyltryptophans with Molecularly Imprinted Polymeric Membranes Containing DVNE Derivatives.

et al. 1998

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Molecularly imprinted polymeric membranes for optical resolution

Cited by 107 publications

References 17 publications

Carboxylated polysulfone membranes having a chiral recognition site induced by an alternative molecular imprinting technique

Carboxylated polysulfone membranes having a chiral recognition site induced by an alternative molecular imprinting technique

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

Chiral Recognition of N-.ALPHA.-Acetyltryptophans with Molecularly Imprinted Polymeric Membranes Containing DVNE Derivatives.

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