Chiral Polyamides Having L-Glutamyl Residue as a Component

DOI: 10.4236/ojpchem.2012.24017   PDF   HTML     3,159 Downloads   5,423 Views  

Abstract

Polyamides with chiral environment were obtained from aromatic diamine, 1,3-phenylenediamine (1,3-PDA) or 1,4- phenylenediamine (1,4-PDA), and N-α-benzoyl-L-glutamic acid (Benzoyl-L-Glu). The optical rotation ([α]D) for 1,3- PDA-Benzoyl-L-Glu was determined to be 3.7 deg cm2 g–1, while that for 1,4-PDA-Benzoyl-L-Glu to be 9.7 deg cm2 g–1. 1,3-PDA-Benzoyl-L-Glu showed adsorption selectivity toward D-Glu and its adsorption selectivity was determined to be 1.68. Contrary to this, 1,4-PDA-Benzoyl-L-Glu showed adsorption selectivity toward L-Glu and the adsorption selectivity toward L-Glu was determined to be 1.33. From those results, those two types of chiral polyamide are expected to applicable to chiral separation or chiral recognition.

Share and Cite:

Y. Ikeuchi, M. Yoshikawa, H. Yoshida, H. Yamanishi and S. Sakurai, "Chiral Polyamides Having L-Glutamyl Residue as a Component," Open Journal of Polymer Chemistry, Vol. 2 No. 4, 2012, pp. 125-131. doi: 10.4236/ojpchem.2012.24017.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] D. Voet and J. G. Voet, “Biochemistry,” Wiley, New York, 1990.
[2] T. McKee and J. R. McKee, “The Molecular Basis of Life,” 3rd Edition, WCB/McGraw-Hill, Boston, 2003.
[3] C. A. M. Afonso and J. G. Grespo, “Recent Advances in Chiral Resolution through Membrane-Based Approaches,” Angewandte Chemie International Edition, Vol. 43, No. 10, 2004, pp. 5293-5295. doi:10.1002/anie.200460037
[4] N. M. Maier and W. Lindner, “Chiral recognirion application of molecularly imprinted polymers: A critical reciew,” Analytical and Bioanalytical Chemistry, Vol. 389, No. 2, 2007, pp. 377-397. doi:10.1007/s00216-007-1427-4
[5] R. Xie, L.-Y. Chu and J.-G. Deng, “Membranes and Membrane Processes for Chiral Resolution,” Chemical Society Reviews, Vol. 37, No. 6, 2008, pp. 1243-1263. doi:10.1039/b713350b
[6] A. Higuchi, M. Tamai, Y.-A. Ko, Y. Tagawa, Y.-H. Wu, B. D. Freeman, J.-T. Bing, Y. Chang and Q.-D. Ling, “Polymeric Membranes for Chiral Separation of Pharmaceuticals and Chemicals,” Polymer Reviews, Vol. 50, No. 2, 2010, pp. 113-143. doi:10.1080/15583721003698853
[7] M. Yoshikawa, J. Izumi, T. Kitao and S. Sakamoto, “Molecularly Imprinted Polymeric Membranes Containing SISE Derivatives for Optical Resolution of Amino Avids,” Macromolecules, Vo. 29, No. 25, 1996, pp. 81978203. doi:10.1021/ma951716v
[8] M. Yoshikawa and J. Izumi, “Chiral Recognition Sites Converted from Tetrapeptide Derivatives Adopting Racemates as Print Moleciles,” Macromolecular Bioscience, Vol. 3, No. 9, 2003, pp. 487-498. doi:10.1002/mabi.200350016
[9] M. Yoshiakwa, Y. Nagai, K. Moriguchi and S. Hiraoka, “Chiral Recogniiton Ability of Oligopeptide Derivatives Consisting of Glutamyl Residues,” Journal of Applied Polymer Science, Vol. 95, No. 6, 2005, pp. 1302-1309. doi:10.1002/app.21307
[10] Y. Sueyoshi, C. Fukushima and M. HYoshikawa, “Molecularly Imprinted Nanofiber Membranews from Cellulose Acetate Aimed for Chiral Separation,” Journal of Membrane Science, Vol. 357, No. 1-2, 2010, pp. 90-97. doi:10.1016/j.memsci.2010.04.005
[11] Y. Sueyoshi, A. Utsunomiya, M. Yoshikawa, G. P. Robertson and M. D. Guiver, “Chiral Separation with Molecularly Imprinted Polysulfone-Aldehyde Derivatized Nanofiber Membranes,” Journal of Membrane Science, Vol. 401-402, 2012, pp. 89-96. doi:10.1016/j.memsci.2012.01.033
[12] M. Nakagawa, Y. Ikeuchi and M. Yoshikawa, “Chiral Separation of Racemic Amino Acids with Novel Polyamide Having N-α-Acetyl-L-glutamyl Residue as a Diacid Component,” Polymer, Vol. 49, No. 21, 2008, pp. 4612-4619. doi:10.1016/j.polymer.2008.08.018
[13] Y. Ikeuchi, M. Nakagawa, M. Yoshikawa, H. Yoshida and S. Sakurai, “Chiral Polyamides Consisting of N-αBenzoyl-L-Glutamic Acid as a Diacid Component,” Journal of Polymer Science Part A: Polymer Chemistry, Vol. 47, No. 10, 2009. pp. 2530-2538. doi:10.1002/pola.23335
[14] T. Hashimoto and M. Yoshikawa, “Chiral Separation of Racemic Mixtures with Chiral Polyamide Membranes Containing Aspartyl Residues in their Main Chains,” Current Nanoscience, Vol. 7, No. 6, 2011, pp. 915-924. doi:10.2174/157341311798220664
[15] M. Hatanaka, Y. Nishioka and M. Yoshikawa, “Polyurea with L-Lysinyl Residues as Components: Application to Membrane Separation of Enantiomers,” Macromolecular Chemistry and Physics, Vol. 212, No. 13, 2011, pp. 13511359. doi:10.1002/macp.201100054
[16] H. Mizushima, M. Yoshikawa, G. P. Robertson and M. D. Guiver, “Optical Resolution Membranes from Polysulfone Bearing Alanine Derivatives as Chiral Selectors,” Macromolecular Materials and Engineering, Vol. 296, No. 6, 2011, pp. 562-567. doi:10.1002/mame.201000396
[17] M. Yoshikawa, M. Maruhashi, Y. Iwamoto and N. Ogata, “Optical Resolution of Racemic Amino Acids through DNA-Poly(4-vinylbenzoyl)trimethylammonium Polyion Complec Membranes,” Polymer Journal, Vol 39, No. 11, 2007, pp. 1193-1198. doi:10.1295/polymj.PJ2007080
[18] Y. Sueyoshi, T. Hahsimoto, M. Yoshikawa and K. Watanabe, “Transformation of Intact Chicken Feathers into Chiral Separation Membranes,” Waste Biomass Valor, Vol. 2, No. 3, 2011, pp. 303-307. doi:10.1007/s12649-011-9066-6
[19] Y. Sueyoshi, T. Hahsimoto, M. Yoshikawa and S. Ifuku, “Chitin Nanofiber Membranes for Chiral Separation,” Journal of Sustainable Agriculture, Vol. 1, No. 1, 2012, pp. 42-47.
[20] “Dictionary of Organic Compounds,” 4th Edition, Maruzen, Tokyo, 1965, p. 2685.
[21] “Beilsteins Handbuch der Organischen Chemie,” 13 IV. Springer-Verlag, Berlin, 1973, p.104.
[22] J. A. Riddick, W. B. Bunger and T. K. Sakano, “Organic Solvents,” 4th Edition, John Wiley & Sons, New York, 1986.
[23] D. J. Walton and J. P. Lorimer, “Polymers,” Oxford University Press, Oxford, 2000.
[24] K. Taniwaki, A. Hyakutake, A. Aoki, M. Yoshikawa, M. D. Guiver and G. P. Robertson, “Evaluation of the Recognition Ability of Molecularly Imprinted Materials by Surface Plasmon Resonance (SPR) Spectroscopy,” Analytica Chimica Acta, Vol. 489, No. 2, 2003, pp. 191-198. doi:10.1016/S0003-2670(03)00760-8

  
comments powered by Disqus

Copyright © 2020 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.