Chiral separation with molecularly imprinted polysulfone-aldehyde derivatized nanofiber membranes

Journal of Membrane Science

Volumn 401-402, Issue , 2012, Pages 89-96

  Sueyoshi, Yuuki ^a   Utsunomiya, Akira ^a   Yoshikawa, Masakazu ^a   Robertson, Gilles P ^b   Guiver, Michael D ^b  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Chiral separation; Electrospray deposition; Membrane; Molecular imprinting; Molecularly imprinted nanofiber membrane; Nanofiber fabric; Optical resolution

Indexed keywords

CHIRAL SEPARATIONS; ELECTROSPRAY DEPOSITION; MOLECULAR IMPRINTING; MOLECULARLY IMPRINTED; NANOFIBER FABRIC; OPTICAL RESOLUTION;

ALDEHYDES; AMINO ACIDS; CHIRALITY; ENANTIOMERS; NANOFIBERS; ORGANIC COMPOUNDS;

MEMBRANES;

ALDEHYDE; NANOFIBER; POLYSULFONE;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; ELECTROSPRAY; ENANTIOMER; ENANTIOSELECTIVITY; ISOMER; MEMBRANE BIOLOGY; MEMBRANE TRANSPORT; MOLECULAR DYNAMICS; MOLECULAR IMPRINTING; MOLECULARLY IMPRINTED MEMBRANE; NANOFABRICATION; PRIORITY JOURNAL;

EID: 84858449496     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2012.01.033     Document Type: Article

References (46)

1. Membrane Handbook 1992, Chapmann & Hall, New York. H. Winston, K.K. Sirkar (Eds.).
2. Mulder M. Basic Principles of Membrane Technology 1996, Kluwer Academic Publishers, Dordrecht.
3. Baker R.W. Membrane Technology and Applications 2004, John Wiley & Sons, West Sussex. 2nd ed.
4. Molecular and Ionic Recognition with Imprinted Polymers (ACS Symposium Series 703) 1998, ACS, Washington, DC. R.A. Bartsch, M. Maeda (Eds.).
5. Molecularly Imprinted Polymers Man-made Mimics of Antibodies and their Applications in Analytical Chemistry 2001, Elsevier, Amsterdam. B. Sellergren (Ed.).
6. Komiyama M., Takeuchi T., Mukawa T., Asanuma H. Molecular Imprinting 2003, Wiley-VCH, Weinheim.
7. Alexander C., Andersson H.S., Andersson L.I., Ansell R.J., Kirsch N., Nicholls I.A., O'Mahony J., Whitcombe M.J. Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003. J. Mol. Recognit. 2006, 19:106-180.
8. Yoshikawa M. Molecular and Ionic Recognition with Imprinted Polymers (ACS Symposium Series 703) 1998, 170. ACS, Washington, DC. R.A. Bartsch, M. Maeda (Eds.).
9. Piletsky S.A., Panasyuk T.L., Piletskaya E.V., Nicholls I.A., Ulbricht M. Receptor and transport properties of imprinted polymer membranes-a review. J. Membr. Sci. 1999, 157:263-278.
10. Yoshikawa M. Molecularly imprinted polymeric membranes. Bioseparation 2002, 10:277-286.
11. Ulbricht M. Membrane separations using molecularly imprinted polymers. J. Chromatogr. B 2004, 804:113-125.
12. Michaels A.S., Baddour R.F., Bixler H.J., Choo C.Y. Conditioned polyethylene as a permselective membrane. Ind. Eng. Chem. Process Des. Dev. 1962, 1:14-25.
13. Yoshikawa M., Izumi J., Ooi T., Kitao T., Guiver M.D., Robertson G.P. Carboxylated polysulfone membranes having a chiral recognition site induced by an alternative molecular imprinting technique. Polym. Bull. 1998, 40:517-524.
14. Yoshiakwa M., Izumi J., Kitao T., Sakamoto S. Molecularly imprinted polymeric membranes containing DIDE derivatives for optical resolution of amino acids. Macromolecules 1996, 25:8197-8203.
15. Yoshikawa M., Izumi J. Chiral recognition sites converted from tetrapeptide derivatives adopting racemates as print molecules. Macromol. Biosci. 2003, 3:487-498.
16. Yoshikawa M., Ooi T., Izumi J. Alternative molecularly imprinted membranes from a derivative of natural polymer, cellulose acetate. J. Appl. Polym. Sci. 1999, 72:493-499.
17. Yoshikawa M., Kawamura K., Ejima A., Aoki T., Sakurai S., Hayashi K., Watanabe K. Green polymers from Geobacillus thermodenitrificans DSM465-candidates for molecularly imprinted materials. Macromol. Biosci. 2006, 6:2010-2215.
18. Burger C., Hsiao B.S., Chu B. Nanofibrous materials and their applications. Annu. Rev. Mater. Res. 2006, 36:333-368.
19. Greiner A., Wendorff J.G. Electrospinning: a fascinating method for the preparation of ultrathin fibers. Angew. Chem. Int. Ed. 2007, 46:5670-5703.
20. Yoon K., Hsiao B.S., Chu B. Functional nanofibers for environmental applications. J. Mater. Chem. 2008, 18:5326-5334.
21. Chu B., Hsiao B.S. The role of polymers in breakthrough technologies for water purification. J. Polym. Sci. B: Polym. Phys. 2009, 47:2431-2435.
22. Agarwal S., Wendorff J.H., Greiner A. Chemistry on electrospun polymeric nanofibers: Merely routine chemistry or a real challenge?. Macromol. Rapid Commun. 2010, 31:1317-1331.
23. Chronakis I.S., Milosevic B., Frenot A., Ye L. Generation of molecular recognition sites in electrospun polymer nanofibers via molecular imprinting. Macromolecules 2006, 39:357-361.
24. Chronakis I., Jakob A., Hagström B., Ye L. Encapsulation and selective recognition of molecularly imprinted theophylline and 17β-estradiol nanoparticles within electrospun polymer nanofibers. Langmuir 2006, 22:8960-8965.
25. Yoshimatsu K., Ye L., Lindberg J., Chronakis I.S. Selective molecular adsorption using electrospun nanofiber affinity membranes. Biosens. Bioelectron. 2008, 23:1208-1215.
26. Yoshikawa M., Nakai K., Matsumoto H., Tanioka A., Guiver M.D., Robertson G.P. Molecularly imprinted nanofiber membranes from carboxylated polysulfone by electrospray deposition. Macromol. Rapid Commun. 2007, 28:2100-2105.
27. Sueyoshi Y., Fukushima C., Yoshikawa M. Molecularly imprinted nanofiber membranes from cellulose acetate aimed for chiral separation. J. Membr. Sci. 2010, 357:90-97.
28. Yoshikawa M., Tanioka A., Matsumoto H. Molecularly imprinted nanofiber membranes. Curr. Opin. Chem. Eng. 2011, 1:18-26.
29. Guiver M.D., Zhang H., Robertson G.P., Dai Y. Modified polysulfones. III. Synthesis and characterization of polysulfone aldehydes for reactive membrane materials. J. Polym. Sci. A: Polym. Chem. 2001, 39:675-682.
30. Riddick J.A., Bunger W.B., Sakano T.K., Organic Solvents 4th ed. 1986, John Wiley & Sons, New York.
31. Taniwaki K., Hyakutake A., Aoki T., Yoshikawa M., Guiver M.D., Robertson G.P. Evaluation of the recognition ability of molecularly imprinted materials by surface plasmon resonance (SPR) spectroscopy. Anal. Chim. Acta 2003, 489:191-198.
32. Kakuchi T., Takaoka T., Yokota K. Polymeric chiral crown ethers. VI. Optical resolution of α-amino acid by polymers incorporating 1,3:4,6-di-O-benzylidene-d-mannitol residues. Polym. J. 1990, 22:199-205.
33. Masawaki T., Sasai M., Tone S. Optical resolution of amino acid by an enantioselective ultrafiltration membrane. J. Chem. Eng. Jpn. 1992, 25:33-39.
34. Aoki T., Tomizawa S., Oikawa E. Enantioselective permeation through poly{γ-[3-(penramethyldisiloxanyl)propyl]-l-glutamate} membranes. J. Membr. Sci. 1995, 99:117-125.
35. Tone S., Masawaki T., Eguchi K. The optical resolution of amino acids by plasma polymerized terpene membranes. J. Membr. Sci. 1996, 118:31-40.
36. Yoshikawa M., Izumi J., Kitao T. Alternative molecular imprinting, a facile way to introduce chiral recognition sites. React. Funct. Polym. 1999, 42:93-102.
37. Yoshikawa M., Fujisawa T., Kitao T. Molecularly imprinted polymeric membranes having EFF derivatives as a chiral recognition site. Macromol. Chem. Phys. 1999, 200:1458-1465.
38. Schultz S.G. Basic Principles of Membrane Transport 1980, Cambridge University Press, Cambridge.
39. Maier N.M., Lindner W. Chiral recognition applications of molecularly imprinted polymers: a critical review. Anal. Bioanal. Chem. 2007, 389:377-397.
40. Xie R., Chu L.-Y., Deng J.-G. Membranes and membrane processes for chiral resolution. Chem. Soc. Rev. 2008, 37:1243-1263.
41. Higuchi A., Tamai M., Ko Y.-A., Tagawa Y., Wu Y.-H., Frteeman B.D., Bing J.-T., Chang Y., Ling Q.-D. Polymeric membranes for chiral separation of pharmaceuticals and chemicals. Polym. Rev. 2010, 50:113-143.
42. Sun Z., Zussman E., Yarin A.L., Wendorff J.H., Greiner A. Compound core-shell polymer nanofibers by co-electrospinning. Adv. Mater. 2003, 15:1929-1932.
43. Li D., Xia Y. Direct fabrication of composite and ceramic hollow nanofibers by electrospinning. Nano Lett. 2004, 4:933-938.
44. Ramakrishna S., Fujihara K., Teo W.-E., Lim T.-C., Ma Z. An Introduction to Electrospinning and Nanofibers 2005, World Scientific, New Jersey.
45. Li D., McCann J.T., Xia Y. Use of electrospinning to directly fabricate hollow nanofibers with functionalized inner and outer surfaces. Small 2005, 1:83-86.
46. Matsumoto H., Tanioka A. Functionality in electrospun nanofibrous membranes based on fiber's size, surface area, and molecular orientation. Membranes 2011, 1:249-264.