Polysulfones with Phenylalanine Derivatives as Chiral Selectors – Membranes for Chiral Separation

Authors

  • Jun Isezaki Department of Biomolecular Engineering, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan
  • Masakazu Yoshikawa Department of Biomolecular Engineering, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan
  • Nanwen Li Department of Energy Engineering, Hanyang University, Seoul 133-791, Republic of Korea
  • Gilles P. Robertson Institute for Chemical Process and Environmental Technology, National Research Council of Canada, Ottawa, Ontario K1A 0R6, Canada
  • Michael D. Guiver Institute for Chemical Process and Environmental Technology, National Research Council of Canada, Ottawa, Ontario K1A 0R6, Canada

DOI:

https://doi.org/10.6000/1929-6037.2012.01.01.1

Keywords:

chiral separation, membrane, optical resolution, permselectivity, polysulfone

Abstract

Polysulfone with a derivative of phenylalanyl residue as a chiral selector (PSf-Ac-D-Phe or PSf-Ac-L-Phe) were prepared by polymer reaction of benzylamine-modified polysulfones with N-a-acetyl-D-phenylalanine or N-a-acetyl-L-phenylalanine. Both polysulfones having a chiral selector gave durable self-standing membranes. The specific rotations of those polymers revealed that the chiral selectors were successfully introduced into the polysulfone. PSf-Ac-D-Phe membrane incorporated L-Glu in preference to D-Glu and vice versa. The chiral separation ability was studied by applying a concentration gradient as a driving force for membrane transport. Permselectivities for those two types of membrane reflected their adsorption selectivities. PSf-Ac-D-Phe membrane selectively transported L-Glu and vice versa. Predicted permselectivities by adopting membrane resistance coincided with the observed ones.

References

Vollhardt KPC, Schore NE. Organic chemistry Structure and function. 3rd ed. New York: W.H. Freeman and Company 1999.

Voet D, Voet JG. Biochemistry. New York: Wiley 1990.

McKee T, McKee JR, Biochemistry – The Molecular basis of life. 3rd ed. Boston: WCB/McGraw-Hill 2003.

Afonso CAM, Crespo JG, Angew Chem Int Ed 2004; 43: 5293-5. http://dx.doi.org/10.1002/anie.200460037 DOI: https://doi.org/10.1002/anie.200460037

Maier NM, Linder W. Anal Bioanal Chem 2007; 389: 377-97. http://dx.doi.org/10.1007/s00216-007-1427-4 DOI: https://doi.org/10.1007/s00216-007-1427-4

Xie R, Chu L-Y, Deng JG. Chem Soc Rev 2008; 37: 1243-63. http://dx.doi.org/10.1039/b713350b DOI: https://doi.org/10.1039/b713350b

Higuchi A, Tamai M, Ko Y-A, et al. Polym Rev 2010; 50: 113-43. http://dx.doi.org/10.1080/15583721003698853 DOI: https://doi.org/10.1080/15583721003698853

Yoshikawa M, Izumi J. Macromol Biosci 2003; 3: 487-98. http://dx.doi.org/10.1002/mabi.200350016 DOI: https://doi.org/10.1002/mabi.200350016

Itou Y, Nakano M, Yoshikawa M. J Membr Sci 2008; 325: 371-5. http://dx.doi.org/10.1016/j.memsci.2008.07.051 DOI: https://doi.org/10.1016/j.memsci.2008.07.051

Sueyoshi Y, Fukushima C, Yoshikawa M. J Membr Sci 2010; 357: 90-7. http://dx.doi.org/10.1016/j.memsci.2010.04.005 DOI: https://doi.org/10.1016/j.memsci.2010.04.005

Sueyoshi Y, Utsunomiya A, Yoshikawa M, Robertson GP, Guiver MD. J Membr Sci 2012; 401-402: 89-96. http://dx.doi.org/10.1016/j.memsci.2012.01.033 DOI: https://doi.org/10.1016/j.memsci.2012.01.033

Ikeuchi Y, Nakagawa M, Yoshikawa M, Yoshida H, Sakurai S. J Polym Sci Part A Polym Chem 2009; 47:2530-8. http://dx.doi.org/10.1002/pola.23335 DOI: https://doi.org/10.1002/pola.23335

Hatanaka M, Nishioka Y, Yoshikawa M. Macromol Chem Phys 2011; 212: 1351-9. http://dx.doi.org/10.1002/macp.201100054 DOI: https://doi.org/10.1002/macp.201100054

Mizushima H, Yoshikawa M, Robertson GP, Guiver MD. Macromol Mater Eng 2011; 296: 562-7. http://dx.doi.org/10.1002/mame.201000396 DOI: https://doi.org/10.1002/mame.201000396

Robertson GP, Guiver MD, Bilodeau F, Yoshikawa M. J Polym Sci Part A Polym Chem 2003; 41: 1316-29. http://dx.doi.org/10.1002/pola.10683 DOI: https://doi.org/10.1002/pola.10683

Riddick JA, Bunger WB, Sakano TK. Organic solvents. 4th ed. New York: Wiley 1986.

Harwood LA, Claridge TDW. Introduction to organic spectroscopy. Oxford: Oxford University Press 1997. DOI: https://doi.org/10.1093/hesc/9780198557555.001.0001

Mizushima H, Yoshikawa M, Robertson GP, Guiver MD. Eur Polym J 2012; 48: 1717-25. http://dx.doi.org/10.1016/j.eurpolymj.2012.07.003 DOI: https://doi.org/10.1016/j.eurpolymj.2012.07.003

Walton DJ, Lorimer JP. Polymers. Oxford: Oxford University Press 2000. DOI: https://doi.org/10.1093/hesc/9780198503897.001.0001

Mulder M. Basic principles of membrane technology. 2nd ed. Dordrecht: Kluwer Academic Publishers 1996. DOI: https://doi.org/10.1007/978-94-009-1766-8

Baker RW. Membrane technology and applications. 2nd ed. West Sussex: Wiley 2004. DOI: https://doi.org/10.1002/0470020393

Kakuchi T, Takaoka T, Yokota K. Polym J 1990; 22: 199-05. http://dx.doi.org/10.1295/polymj.22.199 DOI: https://doi.org/10.1295/polymj.22.199

Masawaki T, Sasai M, Yone S. J Chem Eng Jpn 1992; 25: 33-9. http://dx.doi.org/10.1252/jcej.25.33 DOI: https://doi.org/10.1252/jcej.25.33

Aoki T, Tomizawa S, Oikawa E. J Membr Sci 1995; 99: 117-25. http://dx.doi.org/10.1016/0376-7388(94)00199-9 DOI: https://doi.org/10.1016/0376-7388(94)00199-9

Tone S, Masawaki T, Eguchi K. J Membr Sci 1996; 118: 31-40. http://dx.doi.org/10.1016/0376-7388(96)00071-3 DOI: https://doi.org/10.1016/0376-7388(96)00071-3

Wang H-D, Chu L-Y, Song H, Yang J-P, Xie R, Yang M. J Membr Sci 2007; 297: 262-70. http://dx.doi.org/10.1016/j.memsci.2007.03.055 DOI: https://doi.org/10.1016/j.memsci.2007.03.055

Hazarika S. J Membr Sci 2008; 310: 174-83. http://dx.doi.org/10.1016/j.memsci.2007.10.055 DOI: https://doi.org/10.1016/j.memsci.2007.10.055

Hatanaka M, Nishioka Y, Yoshikawa, M. J Appl Polym Sci in press.

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Published

2012-10-05

How to Cite

Isezaki, J., Yoshikawa, M., Li, N., Robertson, G. P., & Guiver, M. D. (2012). Polysulfones with Phenylalanine Derivatives as Chiral Selectors – Membranes for Chiral Separation. Journal of Membrane and Separation Technology, 1(1), 1–8. https://doi.org/10.6000/1929-6037.2012.01.01.1

Issue

Vol. 1 No. 1 (2012)

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