Chiral Recognizable Properties of Thermosensitive Poly(NIPA-co-NALPE) Hydrogels

Abstract:

A serious of poly(NIPA-co-NALPE) hydrogels containing chiral group (L-Phenylalanine ethyl ester) were prepared by copolymerization of N-isopropylacrylamide(NIPA) and acrylic acid derivatived L-Phenylalanine ethyl ester (NALPE) in ethanol with different feed ratios. The kinetics adsorption approach, isothermal adsorption and chiral separation experiment of hydrogels on D/L-phenylalanine were investigated, and the results showed that the chiral hydrogels exhibited enantioselectivity for D/L-phenylalanine and the absorption capability increased with the rising temperature and increasing contents of NALPE due to the temperature-sensitive NIPA molecular chains and the chiral monomer NALPE, respectively. Furthermore, the poly(NIPA-co-NALPE) hydrogels were also used to separate DL-alanine and DL-tartaric acid, which suggested that the gels are also applicable to other chiral molecules besides DL-phenylalanine and have potential applications in separation of chiral drugs.

• Periodical: Advanced Materials Research (Volumes 160-162)
• Pages: 13-18
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.160-162.13
• Online since: November 2010
• Authors: Jiao Jiao Chen, Lin Jiang, Yi Ping Zhao, Qing Song Zhang, Li Chen
• Keywords: Chiral Recognizable, D/L-Phenylalanine, N-Isopropylacrylamide, Temperature Sensitive

References

[1] Y. Okamoto, T. Nakano: Chem. Rev. Vol. 94 (1994), p.349.

[2] N.M. Maier, P. Franco, W. Lindner: J. Chromatogr. A. Vol. 906 (2001), p.3.

[3] E.R. Francotte: J. Chromatogr. A. Vol. 906 (2001), p.379.

[4] E.L. Izake: J. Pharm. Sci. Vol. 96 (2007), p.1659.

[5] L.D. Taylor, L.D. Cerankowski: J. Polym. Sci: Polym. Chem. Ed. Vol. 13 (1975), p.2551.

[6] Y. Hirokawa, T. Tanaka: J. Chem. Phys. Vol. 81 (1984), p.6379.

[7] K. Heskins, J.E. Guillet: J. Macromol. Sci. Chem. A. Vol. 2(1968): p.1441.

[8] R. Yoshicla, T. Sakai, O. Tamhata: Sci. Tech. Ad. Mat. Vol. 3(2002): p.95.

[9] A. Fucks, F. Gordaninejad: J. Appl. Polym. Sci. Vol. 84 (2002), p.2733.

[10] L. Jiang, J.J. Chen, L. Chen: Int. J Biol. Vol. 2 (2010), p.184.

[11] M.P. Bueno, C.A. Cativiela, J.A. Mayoral: J. Org. Chem. Vol. 56 (1991), p.6551.