Abstract
Bio-based biodegradable hydrogels were prepared by crosslinking microbial homo poly(amino acid), poly(γ-glutamic acid) (PGA), with L-lysine in a one-pot synthesis in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) at 25 °C. The crosslinking was carried out in aqueous solution and the yields of the gels prepared with DMT-MM were higher than those prepared with water-soluble carbodiimide. The water absorption of the PGA gels crosslinked with L-lysine ranged from 300 to 2100 g/g. The water absorption of the PGA gel was affected by the amount of crosslinker and DMT-MM, which had an effect on the crosslinking density of the PGA gel. It was confirmed in a hydrolysis test in a buffer of pH 9 at 37 °C that the obtained gel that was crosslinked with L-lysine by amide bonds was more resistant to hydrolysis than the gel crosslinked by ester bonds. biochemical oxygen demand-biodegradability of the PGA gel crosslinked with L-lysine reached 60% in activated sludge at 25 °C.
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References
Doi, Y., Kunioka, M., Nakamura, Y. & Soga, K. Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate. Macromolecules 21, 2722–2727 (1988).
Hara, T., Anmayr, A., Fujo, Y. & Ueda, S. Elimination of plasmid-linked polyglutamate production by Bacillus subtilis (natto) with acridine orange. Appl. Environ. Microbiol. 44, 1456–1458 (1982).
Shima, S. & Sakai, H. Poly-L-lysine produced by streptomyces. Part III. Chemical studies. Agric. Biol. Chem. 45, 2503 (1981).
Kubota, H., Matsunobu, T., Uotani, K., Takebe, H., Satoh, A., Tanaka, T. & Taniguchi, M. Production of poly(γ-glutamic acid) by Bacillus subtilis F-2-01. Biosci. Biotech. Biochem. 57, 1212 (1993).
Kunioka, M. Biosynthesis of poly (γ-glutamic acid) from L-glutamine, citric acid and ammonium sulfate in Bacillus subtilis IF0335. Appl. Microbiol. Biotechnol. 44, 501–506 (1995).
Choi, H. J. & Kunioka, M. Preparation conditions and swelling equilibria of biodegradable hydrogels prepared from microbial poly(γ-glutamic acid) and poly(ɛ-lysine). J. Environ. Polym. Degrad. 4, 123–129 (1996).
Kunioka, M. & Choi, H. J. Hydrolytic degradation and mechanical properties of hydrogels prepared from microbial poly (amino acid)s. Polym. Degrad. Stabil. 59, 33–37 (1998).
Gonzales, D., Fan, K. & Sevoian, M. Synthesis and swelling characterizations of a poly(γ-glutamic acid) hydrogel. J. Polym. Sci. Part A Polym. Chem. 34, 2019–2027 (1996).
Fan, K., Gonzales, D. & Sevoian, M. Hydrolytic and enzymatic degradation of poly(γ-glutamic acid) hydrogels and their application in slow-release systems for proteins. J. Environ. Polym. Degrad. 4, 253–260 (1996).
Kunioka, M. & Furusawa, K. Poly(γ-glutamic acid) hydrogel prepared from microbial poly(γ-glutamic acid) and alkanediamine with water-soluble carbodiimide. J. Appl. Polym. Sci. 65, 1889–1896 (1997).
Kunioka, M. Biodegradable water absorbent synthesized from bacterial poly(amino acid)s. Macromol. Biosci. 4, 324–329 (2004).
Choi, H. J. & Kunioka, M. Preparation of conditions and swelling equibria of hydrogels prepared by γ-irradiation from microbial poly (γ-glutamic acid). Radiat. Phys. Chem. 46, 175–179 (1995).
Shimokuri, T., Kaneko, T., Serizawa, T. & Akashi, M. Preparation and thermosensitivity of naturally occurring polypeptide poly(γ-glutamic acid) derivatives modified by propyl groups. Macromol. Biosci. 4, 407–411 (2004).
Murakami, S. & Aoki, N. Bio-based hydrogels prepared by cross-linking of microbial poly(γ-glutamic acid) with various saccharides. Biomacromolecules 7, 2122–2127 (2006).
Anastas, P. T. & Williamson, T. C. Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes 1–26 (Oxford University Press, NY, 1998).
Kunishima, M., Kawachi, C., Morita, J., Terao, K., Iwasaki, F. & Tani, S. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: an efficient condensing agent leading to the formation of amides and esters. Tetrahedron 55, 13159–13170 (1999).
Kunishima, M., Kawachi, C., Hioki, K., Terao, K. & Tani, S. Formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM. Tetrahedron 57, 1551–1558 (2001).
Bidlingmeyer, B. A., Cohen, S. A. & Tarvin, T. L. Rapid analysis of amino acids using pre-column derivatization. J. Chromatogr. 336, 93–104 (1984).
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Murakami, S., Aoki, N. & Matsumura, S. Bio-based biodegradable hydrogels prepared by crosslinking of microbial poly(γ-glutamic acid) with L-lysine in aqueous solution. Polym J 43, 414–420 (2011). https://doi.org/10.1038/pj.2010.142
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DOI: https://doi.org/10.1038/pj.2010.142
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