Amino acid-based bioanalogous polymers. Synthesis, and study of regular poly(ester amide)s based on bis(?-amino acid) ?,?-alkylene diesters, and aliphatic dicarboxylic acids

Journal of Polymer Science Part A: Polymer ChemistryVolume 37, Issue 4 p. 391-407 Article Amino acid-based bioanalogous polymers. Synthesis, and study of regular poly(ester amide)s based on bis(α-amino acid) α,ω-alkylene diesters, and aliphatic dicarboxylic acids R. Katsarava, Corresponding Author R. Katsarava Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaCentre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorV. Beridze, V. Beridze Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorN. Arabuli, N. Arabuli Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorD. Kharadze, D. Kharadze Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorC. C. Chu, C. C. Chu Fiber and Polymer Science Program, Department of Textiles & Apparel, & Biomedical Engineering Program, Cornell University, Ithaca, New York 14853-4401Search for more papers by this authorC. Y. Won, C. Y. Won Fiber and Polymer Science Program, Department of Textiles & Apparel, & Biomedical Engineering Program, Cornell University, Ithaca, New York 14853-4401Search for more papers by this author R. Katsarava, Corresponding Author R. Katsarava Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaCentre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorV. Beridze, V. Beridze Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorN. Arabuli, N. Arabuli Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorD. Kharadze, D. Kharadze Centre for Medical Polymers and Biomaterials of Ministry of Health, and Institute of Molecular Biology & Biophysics of Georgian Academy of Sciences, P.O. Box 24, 380079, Tbilisi-79, GeorgiaSearch for more papers by this authorC. C. Chu, C. C. Chu Fiber and Polymer Science Program, Department of Textiles & Apparel, & Biomedical Engineering Program, Cornell University, Ithaca, New York 14853-4401Search for more papers by this authorC. Y. Won, C. Y. Won Fiber and Polymer Science Program, Department of Textiles & Apparel, & Biomedical Engineering Program, Cornell University, Ithaca, New York 14853-4401Search for more papers by this author First published: 21 January 2000 https://doi.org/10.1002/(SICI)1099-0518(19990215)37:4<391::AID-POLA3>3.0.CO;2-ECitations: 165AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Abstract The purpose of this research was to synthesize new regular poly(ester amide)s (PEAs) consisting of nontoxic building blocks like hydrophobic α-amino acids, α,ω-diols, and aliphatic dicarboxylic acids, and to examine the effects of the structure of these building block components on some physico-chemical and biochemical properties of the polymers. PEAs were prepared by solution polycondensation of di-p-toluenesulfonic acid salts of bis-(α-amino acid) α,ω-alkylene diesters and di-p-nitrophenyl esters of diacids. Optimal conditions of this reaction have been studied. High molecular weight PEAs (Mw = 24,000–167,000) with narrow polydispersity (Mw/Mn = 1.20–1.81) were prepared under the optimal reaction conditions and exhibited excellent film-forming properties. PEAs obtained are mostly amorphous materials with Tg from 11 to 59°C. α-Chymotrypsin catalyzed in vitro hydrolysis of these new PEA substrates was studied to assess the effect of the building blocks of these new polymers on their biodegradation properties. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 391–407, 1999 REFERENCES AND NOTES 1 Törmälä, P. Adv Mater 1992, 4, 589. 2 Vainiopää, S.; Rokkanen, P.; Törmälä, P. Prog Polym Sci 1989, 14, 679. 3 Nathan, A.; Kohn, J. In: Biomedical Polymers: Design-to-Degrade System, S. W. Shalaby, Ed.; Hanser publishers: Munich, 1994; p. 117. 4 Drobnik, J. Adv Drug Delivery Rev. 1989, 3, 229. 5 Sadesh Kumar, G. Biodegradable Polymers—Prospects and Progress, Marcel Dekker, Inc.; New York, 1987. 6 Sela, M.; Katchalski, E.; Olitzki, A. L. Science 1956, 123, 1129. 7 Stewart, F. H. C. Aust J Chem 1969, 22, 1291. 8 Ridge, B.; Rydon, H. N.; Snell, C. R. J Chem Soc Perkin I, 1972, 2041. 9 Goodman, M. 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